Real Estate Strategy in 2026: Where Smart Investors Are Winning

“Today’s market takes actual skill. The math has changed. Everything’s gone up, expenses, debt, and everything. So you really got to focus on cash flow.” — Daniel Roccanti, CPA

In this James Moore Live episode, Daniel Roccanti, CPA at James Moore & Company, breaks down what it takes to succeed as a real estate investor in 2026. From cash flow fundamentals to portfolio re-underwriting, the conversation covers the strategies separating smart operators from those struggling to keep up.

The discussion covers some of the most pressing questions real estate owners are facing right now: how to think about offense versus defense, where profit optimization actually comes from, and why financial visibility matters more than ever in an uncertain market.

Resources

• Real Estate Services | James Moore & Company
• Your CPA’s Take on Real Estate | James Moore
• Watch the Full Episode on YouTube

Full Transcript

[00:02] Host: Hi everyone and welcome to the James Moore LinkedIn Live. Today we are here with Daniel Roccanti. Hi Daniel, how are you?

[00:06] Daniel Roccanti: Hi, it’s good to be back.

[00:08] Host: Good. So today’s episode is real estate strategy in 2026, where smart investors are winning, because I think a lot of people talk about the failures. Sometimes it’s nice to focus on the successes that people are having and some of your advice I think would be great too. So the first question is what’s the biggest financial shift real estate owners are dealing with right now, and why are so many unprepared?

[00:34] Daniel Roccanti: When we think about this market, you were mentioning before, like why does it feel like real estate is so tough right now? I think it has more to do with where real estate was a few years ago compared to where it is now. Before, it just made this shift where it moved from kind of this growth appreciation market to more of a stable cash flow market. And so back then you could do whatever you wanted. Just buy real estate and it’s going to go up. You didn’t even have to buy a cash flowing deal. And so for a long time it just felt like anyone going into real estate didn’t need to be good, didn’t even need to be efficient and they still won. Today’s market takes actual skill. The math has changed. Everything’s gone up, expenses, debt, and everything. So you really got to focus on cash flow. So when I’m talking to my clients, I’m like, have you run the numbers? Does this cash flow? Does it cash flow if the market gets worse? I know it’s hard to believe this sometimes when you’re like, the market can’t get worse. It absolutely can get worse. Just look at history, talk to a few people from 10, 15 years ago and they’ll tell you how it got a lot worse. It can get worse. I don’t know if it actually will, but you need to map that out in your scenario. Go back from the method of where my property that I buy is going to double in value in five years, to a more sustainable appreciation amount, but really this is a cash flowing asset and it needs to be supported by its cash flow.

[02:12] Host: Absolutely. So are you seeing more investors play offense or defense in today’s market, and what should they be doing instead?

[02:40] Daniel Roccanti: So I would say it’s definitely a more defensive market and there are lots of investors out there playing pure defense right now. But really what you need to be doing is playing selective offense. If you’re into real estate, you should never ever 100% not buy. Now you might look and not buy. That’s absolutely fine. But you should always be looking and running the numbers, because the market will kind of tell you before it turns. So even if you’re not really looking, by running the numbers, if you’re out of the game altogether, you’re going to figure it out too late. The people that are in the market, still doing their job, still looking at deals, are going to figure it out before you and they’re going to get the better deals because of it. So you want to be a smart investor here and you want to play selective offense. Keep looking at deals, keep running the numbers, just don’t pull the trigger if the numbers don’t make sense. You need to justify that it’s still a good purchase. What happens if rent gets slower? Expenses keep going up. Make sure it still cash flows. You don’t want what I call the investor itch. Anyone investing in real estate, they just get that itch and they just haven’t bought in a while and they’ll make a bad decision and buy, or they get really scared and then they won’t buy anything ever again because they had one bad deal that went the wrong way. Neither one of those is too extreme. You always want to be in. It’s just probably a little bit more defensive right now, but keep that offensive and selective.

[03:57] Host: Yeah. And you know, it made me think of, okay, let’s say 10, 15 years ago, especially in South Florida, real estate was like, you have extra cash, just go buy. You’re going to triple whatever you invest. And I think sometimes now, like you said, it’s not necessarily like that anymore. You have to be smart. You have to know. And it’s not as wild west fun to make those moves. But having someone like you advise them on the right things to do would show profit.

[04:43] Daniel Roccanti: Absolutely. And a good investor, they’ll run their own numbers, but a lot of them will still run it by me. What do you think? What am I missing here? And that’s a good advising opportunity to give my input on the deal as well.

[04:57] Host: Absolutely. So what does profit optimization actually look like for real estate owners beyond just cutting costs?

[05:09] Daniel Roccanti: So I think when people think profits, they’re just like, let’s cut the costs. And you’re really profit driven. I mean, this is business. Everyone’s profit driven. The whole point is to make profit. If we don’t, why are we doing it? But when your sole focus is on profit and you’re not thinking long term, you can actually hurt your profits in the long term. So when you’re thinking about profit optimization, you really want to understand, am I improving the quality? Am I doing everything? Am I thinking about the rents? Are the rents at actual market? Can I up my rents? If I improve my property, does that actually make it a more valuable property? CapEx is an expense, but I actually might make my investment and my profitability better in the long term by investing in my properties. What I see with real estate is people sometimes buy a nice property but they’re just sucking it dry of every profit and they’re not reinvesting back into it. All that delayed maintenance, deferred maintenance, and then it looks outdated, it can’t even come close to getting the rents, and then it gets to be just such a big problem where they have to put a crazy amount of money back into it or they just have to sell it at a discount. So you really want to make sure when you’re doing profit optimization, you’re looking at rents, expenses, and how you’re keeping your property up to date so that people want to rent it. You want to still be one of the top ones they’re looking at and not looking like a 1970s apartment complex that’s outdated. You need to keep it up to date because in the long run, you’ll actually make more profits by sometimes spending a little bit more money year to year.

[06:48] Host: Absolutely. How important is cash flow visibility in today’s market and what are people getting wrong?

[07:07] Daniel Roccanti: I think we really need to go back to cash flow. It’s kind of everything right now. We really got used to in the real estate community just buying properties because they appreciate. In today’s market, the numbers need to make sense. Don’t make the mistake of just because it makes numbers on accounting or your books, it doesn’t actually cash flow. It needs to cash flow and it needs to do that first before everything else. So you really need to be going in and doing what your net operating income is, going in there and seeing the visibility of your company. We’ve talked about this before. 13-week cash flows, 12-month rolling cash flows. You really need to be understanding what happens if the market turns. Am I still going to be cash flowing no matter what I’m seeing? If you’re just going out there blindly and hoping for the best, you’re going to actually get something unexpected that could ruin that property and ruin your investment. You just need to be making sure the property cash flows in the current and that it will continue to cash flow, and if something changes, you’re able to catch it before everyone else does.

[08:07] Host: Absolutely. And this next question, I actually think you could write a whole blog series on because I think this is on everyone’s mind, but what role does timing play right now? Are investors moving too fast, too slow, or just guessing?

[08:30] Daniel Roccanti: There’s not really a lot of moving too fast or too slow. That’s different for everybody. It really comes down to you need to get out in front of everything. What I see people do is say, all right, I have debt that’s coming up, but they don’t think about it until the debt is coming up right then. You need to be out in front of that. You need six months, sometimes even 12 months, in today’s economy of getting there and talking to your lenders. If you start talking to them 30, 60 days before it becomes due, it’s too late. You’ve limited your options. So really, when it comes to investors, it’s not that you’re too fast or too slow. It’s that usually you don’t think about it until it’s too late. You need to really understand that your timing just needs to always be, all right, debt’s coming up six months from now, I need to be reaching out to my lenders. Tax planning always seems to be a little too late when you want to do it. It needs to be well out in front of you. When we’re talking about renovations, you need to be thinking about that before the renovations will ever need to happen. What the cost will be, coming back to taxes, maybe I’m looking at selling, do I want to do a 1031 exchange? Are you thinking about it when you’re selling it or are you thinking about it before the property’s even for sale? What are my options with this property and does it make the right decision for me? You just want to always make sure that you’re proactive planning so that you’re not running into things too late. You’re really limiting your options if you do.

[10:00] Host: Absolutely. What’s one financial move smart real estate operators are making right now that others aren’t?

[10:20] Daniel Roccanti: So in today’s market, a lot of investors are on the sideline right now. And that’s not necessarily a bad thing, but if you’re on the sideline, you have time. Re-underwrite your entire portfolio. Like, if you were to buy, would you buy this portfolio today? If you had a clean slate, would you buy it? Reanalyze your whole portfolio. You’ll probably be surprised. Go back today and say, all my properties, would I buy this today in my current situation? What’s my real return? What’s my real cash flow on this? What happens if the market does get worse? What happens if my debt and I have to refinance, is it still going to cash flow then? So really what you want to do is reassess your current situation, not in the market when you originally purchased it, but in today’s market, to really understand is this my most efficient portfolio? Sometimes if you have a terrible asset that’s not cash flowing, now you have at least an idea. Should I get rid of it? Find a new one? Are there ways I can improve it? But if you’re just sitting on the sideline waiting for the market to get better and doing nothing, then you’re really just doing what everyone else is doing, which is just hoping the market saves you. Real estate is great because of the control you have. This isn’t buying a stock. I don’t buy a stock in Apple and then just hope they do well. This is your controlling asset. You control it. The market does have a play here, but your control matters so much more and you can make this a great investment, or an okay investment, or even a bad investment.

[12:00] Host: Absolutely. So the last question is, if you were advising a real estate owner today, which you do, what’s one thing that you would tell them to focus on for the next 12 months?

[12:26] Daniel Roccanti: I would say let’s focus on your financial visibility. This all kind of has the same recurring theme here, but really go back and look at each asset. Look at the cash flow. Look at the debt. Look at your CapEx. Look at your taxes. Look at what your break-even occupancy is. What is your upcoming risk? I really want to understand each property and financially how well they’re doing. What’s the financial health of each asset? Then I want to know what my options are. You always need to know what your options or your choices are before you ever need them. So that could be refinancing, restructuring, selling, bringing in new investors, doing a 1031 exchange. That could even be, do I need to adjust my distributions? You really need to get out in front of that. If you have investors or even just a property you own, usually you’re expecting a certain amount of money every year. Well, maybe we need to actually pull back on that and reinvest into the property so that we can have those distributions more. We might have to put some things on pause. You really want to understand, because if you don’t know what your options are, this is when people get in trouble. An incident happens and you’re out of options. And when you’re out of options, you’re basically doing whatever the market gives you, or sometimes unfortunately going bankrupt, or just losing the trust of your investors or other people in the real estate industry. You really want to make sure you know where the health of your properties stands and what options you have if something comes up, so that you can deal with any situation the market throws at you.

[13:49] Host: Absolutely. I think sometimes it can feel overwhelming, especially when you see all these homes going up in price and you’re an investor thinking, oh, this is great, and then it’s like, no, I can’t afford this. But I think it’s great to have you, Daniel, as an advisor. And I think if anyone is in the process right now of looking to invest or needs solid advice, reach out to Daniel, his LinkedIn is Daniel Roccanti and James Moore. He’s a great guy, fun to talk to.

[14:30] Daniel Roccanti: Great. It was a pleasure again.

[14:32] Host: Yeah, talk to you soon. Thanks.

Watch the full conversation with Daniel Roccanti on the James Moore YouTube channel.

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