4 Rookie-Friendly Ways to Find Great Real Estate Deals in 2026 (Rookie Reply)

Ashley:
You’re ready to start investing, but now you’re staring at the three questions every rookie hits first. How do I actually learn this? Where do I find a real deal? And if I finally have some money saved, what should I

Tony:
Do with it? Today’s questions come straight from the BiggerPockets forums, and they’re still all about getting out of the research phase without rushing into a bad first thing.

Ashley:
This is the Real Estate Rookie Podcast. I’m Ashley Kehr. And

Tony:
I’m Tony J. Robinson. With that, let’s get into our first question. So question number one today comes from Omi in the BiggerPockets forums. And Omi says, “I’m 23 and I’m looking to build a buy and hold rental portfolio in the Midwest with markets like St. Louis, where I’m based, Kansas City, Indianapolis, Cleveland, and Columbus on my radar. I’ve started doing my homework. I’ve read quite a bit, listened to podcasts, and started talking with investors and professionals, but I keep landing on the same question. What’s actually the best way to learn this? Well, instead of piecing it together from a bunch of different threads. For those who started from zero, did you pay for a course or coaching or go the free content plus trial and error route? If you paid, what was it for and was it actually worth it? If you didn’t, which books, podcasts, YouTube channels and forums actually moved the needle for you?
Bonus question. If you were 23 and starting today, knowing what you know now, what’s the first move that you would make? Not fishing for a shortcut. I know experience is the best teacher. I just want to invest my time and money wisely, whether that’s through self-study, mentorship, or equality course alone. I don’t just want to blow three to 5K on a course that BP could have replaced or spend six months reading and missing something a good course would’ve flagged on day one. It’s a great question and probably one of the more heated debates in the BiggerPockets forums. And I’ll give my take first, guys, is that I think like anything in life, there’s probably pros and cons to paying for assistance and different people need different resources. Now, what I will say is that regardless of whether or not you choose to go join a course, get a mentor, whatever it may be, you still need that strong foundational knowledge.
You still need to be listening to the Real Estate Rookie Podcast. You still need to be reading books, watching the YouTube videos and laying a strong foundation. I don’t think anything replaces that. But once you have that foundation laid and you’re thinking about actually taking that next step, I think there’s a couple of questions to ask yourself to say, does paying for guidance actually make sense? The first question that I’d ask yourself is, how much time are you willing to invest and how many mistakes are you willing to make to get it right on your own? Because as much as you watch YouTube videos, as much as you can read books, it’s still difficult at times to take that information and distill it in a way that makes sense for your unique situation. And there’s no feedback loop there from the author to say, “Hey, Ashley and Tony, if you get stuck here, here’s what I would actually do.” You have to infer what the right next step would be based on the knowledge that you’ve gained.
So that’s the first piece is how much time are you willing to spend and how many mistakes are you willing to make? And then I think the second piece is the capital. If you are very capital constrained, I would never want someone spending their only $5,000 on the course and then rebuilding their capital, try and go out and get the deal done. You’ve got to make sure the capital’s there to cover that and still have enough leftover to go buy the actual deal.

Ashley:
For me, I didn’t start with a course or coaching. I was pretty much solo. And then that was in 2013. And then 2017, I found BiggerPockets, went into the forums, was just consuming information. And I was able to triple my portfolio in that year just from reading and learning from what other investors were posting. I don’t even think I posted that much myself, but just reading through the forums. So that was such a big help for me. And I think you need to, before you even decide if you should do a course or if you shouldn’t, you need to ask yourself a couple questions, not even regarding real estate or courses, but how do you learn? Think about back when you were in school or maybe you’re still in school. Was it a torture to sit through a class and listen to the teacher talk?
Do you love to read? Is it easy for you to read, to scroll and read the news on your phone, sit with a book? Are you more engaged when it’s a bunch of people such as doing a Zoom call where there’s a lot of other people on the call and they’re asking questions and you’re engaged into the chat? What is the best way that you learn? For me, I went to a seminar about a month ago. It was horrendous for me because I was taken back to my college days sitting in a class from. We were there from 8:00 AM to 6:00 PM those two days I was there and I could not sit still. I could not focus. I dreaded it. Okay? I realized once again, it was a great reminder. I do not learn that well. So I can’t attend courses and things like that where you’re in a classroom setting and you’re sitting just listening to someone talk and talk and talk and talk.
If it was a workshop setting where it’s hands-on, I can learn that way. I know that it’s engaging. You’re actively doing something that I can handle. Zoom calls, I can also handle Zoom calls if it’s not a webinar format. I can’t sit there and I can’t watch a webinar. If it’s engaging where there’s people coming onto the call to ask questions, if there’s a chat going and you’re being engaged into the call, that I can do. Self-paced stuff, I cannot do. I used to try to take the real estate exam to get my real estate license. I started the online course probably about four times. I paid the 99 fee to restart the course and I just couldn’t do it. I wouldn’t make the time for it. It wasn’t priority. So I can also do self-paced courses. So really think about yourself and how you actually learn.
And also who the instructor is, what the topic is, things like that, and if that will actually benefit you. But I think taking that first step too is how do you learn? And maybe scrolling forums and things like that is actually going to be more beneficial than paying for a course that’s self-paced where you’re supposed to watch the videos, but you never actually do it.

Tony:
I think the last thing I’d add is that some of the biggest jumps in my life, both personally and professionally, came when I hired an actual coach. I got in the best shape of my life when I hired a fitness coach to tell me what to eat and when to work out and when to sleep and when to do all those things. Even as a business owner, like entrepreneurial, not even just real estate, but as an entrepreneur, I think my biggest leaves came when I invested into the right coaching. And so I’m going to sit down and look at my specific situation and say, “Hey, here’s what you should do next.” And as I look at the people who are far more successful than I am, they spend even more money on coaching and people telling them what to do than I do. So I think my aspiration is to spend even more of my money on a coach who’s done what I’ve done telling me exactly what it is that I need to do because I’ve seen that be the path for success.
Now you’ve got to vet the person, got to make sure that the pedigree is there. But generally speaking, the folks who have found more success than I have, have also invested more themselves than I have as well.

Ashley:
And go into it with a plan of what you want to get out of it. So what do you want to get out of whatever course or coaching that you’re doing? And make sure that’s what you’re actually going to get out of the course that you sign up for. Coming up, learning is great, but how do you actually find your first property when Zillow feels picked over and every good deal seems to go to someone else first? That’s next. All right, so we’ve talked about how to learn without getting stuck. Now let’s talk about where deals actually come from. Our second question comes from Samuel in Minneapolis. “Hey y’all, I’m a new investor looking for leads on potential flips or Burr properties. I’ve joined a few Facebook groups and I’m on Zillow a little too often, but in my experience, the best opportunities often come from the right connections.
So here’s my ask. Where have you found opportunities to invest? Can you recommend anyone I should connect with?

Tony:
“First, let me answer for you, Ashley, because you would say in line at the grocery store, at the mailbox, checking the mail, at my kids’ football games. Those are the places that Ashley goes to find all of her best deals.

Ashley:
I always say I’m not going to buy anything. And then the perfect deal just comes to me, which is not a strategy to actually find deals. Those are just bonus opportunities that come up. But that happens from networking and talking about what you’re doing and not talking about going to meetups where there’s other investors, but also your friends and family and people you’re around, letting them know what you do, what you’re looking for and things like that. And deals will come to you over time. Maybe it’s a bit of manifesting. I don’t know. I’m not a big manifester, but –

Tony:
I guess I’m not manifesting hard enough. I think for me, and it’s a great question. And look guys, good deals are, we call them good deals because they’re not abundant.You’ve really got to do some legwork to get there. But if I’m a new investor starting out, I think what you laid out here, Samuel, is a great starting point. Going into the local Facebook groups, posting what your buy box is, who it is, what areas you’re focused on, price points, things like that. And you just go in there once a week and repost that same message across all the Facebook groups. And you’ll just, by default, wholesalers are in those groups just scraping, looking for people that they can go message. I think that’s an easy way. I think getting active in your local real estate meetup scene, super helpful as well. A lot of times you can connect with the big wholesalers and maybe the newer guys on the scene who are still hunting for their first deal.
And they’re hungry for a buyer. They’re asking the same question, but how do I find buyers for these deals that I’m finding as a wholesaler? So I think getting into the room, getting into the physical space with other investors will be big. And then if you can meet maybe other flippers or Burr type investors in your market, they also don’t have unlimited capital. So sometimes maybe a deal comes across their desk or like, it doesn’t quite fit my buy box or I’m maxed out right now. Hey, let me pass this off to Tony Nash and see if they want it. Or maybe they’re open to sharing who their wholesaler is. So I think building your connections both digitally in the Facebook groups, great place to start, but also kind of pounding the pavement in real life and trying to meet people and shake hands would be a good way to get started as well.

Ashley:
I’m also very anti, there’s no deals on the MLS because I’ve found lots of deals on the MLS. And I’m going to challenge you to like, why are you saying there’s no deals on the MLS? Is it because there’s physically no properties listed for sale that fit your criteria? Or is it because the asking price when you analyze the numbers doesn’t work? It’s a negative cash flow. Because you don’t actually know if it’s a good deal or not until you make an offer to see if your offer is accepted. So remember a property, what it’s listed for doesn’t mean that’s what it’s going to sell for. You can actually buy a property for less money. So you don’t actually know if it’s a good deal or not, unless maybe there is maintenance, rehab, things like that doesn’t fit your criteria that needs to be done.
But as far as if you’re saying that because it’s listed at a higher price point than you think it’s worth, then you need to run the numbers, go to the BiggerPockets calculator reports and play around and change the purchase price until the numbers do make sense. So that means you have to offer $20,000 less, $50,000 less. In a lot of markets right now across the country, we are in a buyer’s market. One thing that I really like to do is I go on Zillow and I like to sort the properties by newest. So the ones that have just recently hit the market, so by days on market. And then I go to the very last page and I look at what has been sitting for a long time. And usually those are more motivated sellers than somebody that just hit the market. I go and I look at the pricing.
So okay, how long has it been on the market since they listed it? Have they done any price drops? How many have they done? Something I’m seeing happen a lot in two vacation towns that I keep my eye on. One is a ski resort town, one’s a lake house town, is I am seeing them list the property and then de-list it over the winter and then list it again. Some of these properties have been listed, this is their third summer being listed. And you wouldn’t know that because the days on market only shows the most recent listing. You have to actually go back and look at the history of the property that’s available on Zillow. But I think that’s a great starting point for actually looking at the properties on Zillow to find some deals.

Tony:
Ash, I couldn’t agree more. I just want to highlight that is that right now, at least as of this recording, we’re talking like summer 2026. Right now is a great time to ignore the purchase price. Whatever the list price is on any properties you see on the MLS, completely ignore it and go in with whatever numbers make the most sense for you. Sellers are having a little bit of a hard time right now. And I know that because I’m selling a property right now, a flip that we’ve been sitting on for way too long. So sellers are not having the best time right now, but you can use that as leverage. And if somebody came to me with a really kind of insulting offer, I would at least consider it today because it’s like I’ve been sitting on this property for too long. And I’m sure there’s a lot of sellers who feel that same way.
So don’t worry about what the list price is. Focus on where this number makes sense for you and then just offer even below that number. All right guys, we’re going to take a quick break, but when we’re back, a listener has what a lot of rookies want, free housing and money saved. The question is whether to buy now, keep saving, househack, or try an out-of-state rental. We’ll walk through it right after this. All right guys, welcome back. Our last question comes from Derek. And this one has him at a bit of a crossroads and a bit of a sicky situation, but here’s what Derek says about what’s going on in his life. So he says, “My wife and I just got married and have an interesting situation in regards to real estate. We currently live in a tiny house for free as part of compensation for my job.
While we are extremely grateful for the free housing, it’s starting to become too small and we’re hoping to upgrade toward a bigger space in the near future, especially as we’re hoping to have children within the next two to three years. For context, we can comfortably put down 30K on a property and qualify for state assistance of an additional 15K down payment. And we make about 95K annually combined. So we have a few options. Option number one is that we build an additional tiny house and join them together at our own expense. This would be relatively inexpensive, about 15K, but it would be a sunk cost. It would let us continue to enjoy free housing for the next few years and save more for a down payment, but would be extremely challenging to have kids in. Number two, buy a small single family in our area.
We live in Rhode Island and the housing market is essentially out of our price range everywhere except for those areas where we do not desire to live. So we could buy a small single family, live in it for a few years with the hope to sell the refi into something bigger while keeping it to rent as a long-term rental. At least we will be gaining equity with this option, though I worry we do not have enough saved for this to make sense given how expensive our market is. Option three, buy an out-of-state short-term rental. This is the most interesting idea to me as out-of-state properties are more affordable and the upside is much stronger. We’ve been looking at upstate New York. However, this option means we are stuck in the tiny home we live in until we have enough equity to either borrow against the SDR or sell it.
And then option four is house hacking a duplex. This I would love to do. However, I’ve been unable to find any duplexes that we can afford in our area, though I do look daily. All right, so just to recap, because this is a great question. So they’ve got free housing right now, but the place is really, really small. They’re thinking about either putting 15K to add on to their existing footprint, but they wouldn’t own that at all. Once they’re done with the job, they lose that. They buy a single family in their current area and a place they don’t want to live in. It’s not the best area. They buy an out-of-state short-term rental or they house hack something maybe in their local area as well. Those are all good options. Or I guess each option kind of has its own merit. One of them I’d rule out immediately, and I’m curious if you say the same thing, Ash, but the 15K to add onto the tiny house that isn’t theirs, I wouldn’t do that.
I feel like that’s not a good use of their funds to dump it into an asset that they don’t actually control. What’s your take on that first one?

Ashley:
100% agree. You’re not going to get that money back. You’re not going to get any tax advantage to doing that. I would say no, because also what is the guarantee that you actually can live there for a few more years? Your job could go away. They could not renew your lease on the property. I’m not sure how it’s set up with work, but jobs come and go. There’s no such thing really as job security in a lot of cases. So I would agree with you on that, Tony.

Tony:
So of the other options we have left, buying a small single family in their area, but in a part of town they don’t want to live in, buying an out-of-state short-term rental that’s more affordable or house hacking. And I think I questioned the house hack because if they can’t afford a small single family, would they be able to afford a small multifamily in that area? So I wonder if they kind of fall into the same sicky situation, but between those three options, which one are you leaning more so toward?

Ashley:
Well, I’m actually going to eliminate the out-of-state short-term rental. And I’m going to do that because this doesn’t solve their problem. They want more space. So even if they went and bought the short-term rental, I feel like they’re still not going to be trying to achieve what they actually want is to get a bigger house, but not have to pay full price for it, I guess. I’m actually going to lean towards house hacking a duplex. And when they say they can’t afford that, I’m curious as to how much has gone into actually looking at how much rent they would receive for the other side of the property and by doing different strategies. So did they compare with what long-term rent would be, what renting by the room would be for that other unit, what a short-term rental would take in that other unit? So I’m going to say house hacking a duplex and also why can’t they afford it in their area?
Have they looked at all of the options of renting out that other unit? I’m

Tony:
Going to throw a curve ball and give them an option that they didn’t even list here. I think the fact that they’re three years away from really, really needing the space, I try and stretch that a little bit longer because it’s free housing. They’re living for free, which oftentimes is going to be your biggest expense. And with the 30K that you’ve got saved up, I wonder if instead you could take that, maybe go flip some houses either locally in your area or maybe even try and do it remotely somewhere else where your budget will stretch and use that 30K as a foundation to get a bigger chunk of cash back on one or two house flips. And now with the money you’re saving from the rent, in addition to the money that you’re making from the flips, can you maybe now in the next 24 months go out and buy a bigger property that kind of checks all those boxes in the actual part of town that you want?
So I think let’s leverage the free housing, but let’s go deploy that capital in a way that’s going to multiply two or three X over the next couple of years. If

Ashley:
You’re in that beginner stage, today’s episode should be permission to slow down in the right places and speed up in the right places. Don’t rush into the wrong deal, but also don’t spend the next year only learning either. You have to take some action. This has been an episode of Real Estate Rookie. I’m Ashley. He’s Tony and we’ll see you guys on the next episode.