Tax Planning Beyond April: A Year-Round Strategy for Real Estate Owners
Originally published on October 1, 2026
“The real loss is an opportunity cost, because most high-value decisions have to be made before the end of the year.” — Daniel Roccanti
Tax season may be over, but the planning window is just getting started. In this episode of Your CPA’s Take on Real Estate, Daniel Roccanti sits down to break down why year-round tax strategy matters for real estate owners, and what most people miss by only thinking about taxes once a year.
The conversation covers 1031 exchange alternatives, how SALT limitations are playing out differently by state, why mid-year is actually the best time to plan, and how bookkeeping quietly affects both your tax bill and your audit risk. It closes with a simple question every owner should ask before year-end: would you buy this property again today?
Resources
Full Transcript
[00:02] Faith: Hi everyone and welcome. Today I am here with Daniel Roccanti. Hi Daniel, how are you?
[00:02] Daniel: Hi Faith.
[00:05] Faith: All right, so let’s get right into it. We got a lot of questions to cover. Today’s topic is tax planning beyond April, year-round strategies for real estate owners. The first question is, why is reactive tax filing costing real estate owners more than they realize?
[00:22] Daniel: So I think a lot of taxpayers only think about taxes one time a year. And it’s like, I got to file a tax return. And so that kind of mindset is really limiting your opportunities. The real loss is an opportunity cost, because most high-value decisions have to be made before the end of the year, and it takes time for that.
[00:57] So if you’re only thinking about taxes and strategizing around that after the year’s already done, you’ve probably missed out on a significant amount of opportunities and you don’t even know it. It’s really important that you understand you need to be thinking about tax strategy year-round, not just during tax filing season. And now that tax filing season is over, this is a great time to start thinking about 2026 and beyond.
[01:17] Faith: Right, exactly. Are there strong alternatives to the 1031 exchange owners should consider?
[01:25] Daniel: So the 1031 exchange is very powerful. Most people in real estate already know what that is. I can basically sell my real estate and buy a new piece of real estate tax-free, deferring that gain. But it’s not always the best answer, there are strict guidelines around it.
[01:44] One alternative is technically still a 1031 exchange, but you can exchange into a DST, a Delaware statutory trust. Instead of buying and managing the property yourself, you’re owning a portion of real estate that somebody else manages. It’s a great opportunity for switching from active to passive real estate investing, especially if you’re getting up there in age, don’t really want to take care of it, and are starting to think about the next generation who also don’t want to take care of real estate. It’s a great way to avoid selling, avoid the tax hit, but still fit into your overall plan.
[02:25] There’s also installment sales. It’s not going to defer the gain forever, but that way I don’t have to pay the whole thing at once. I can sell it on an installment sale and get paid out over time, like owner financing.
[02:43] Qualified opportunity zones are back too. If you’ve seen the new tax bill that came out last year, this is going to be huge starting in 2027, opportunity zones 2.0 is what they’re calling it. The old opportunity zones phase out, this new one starts, and it comes with a lot of the same benefits along with some new ones.
[03:03] And then one that gets overlooked a lot is what we call a Section 721, or UpREIT, contribution. You can contribute property into another partnership tax-free. So instead of just selling the property and buying a new one on your own, like a DST, you can find a syndication or a real estate fund out there and contribute your property in exchange for ownership in that fund, doing this tax-free contribution into it.
[03:49] Faith: Oh, that’s amazing, I think you just taught me things. Wow. How are SALT limitations impacting real estate investors right now?
[03:56] Daniel: SALT limitations are very geographical. If you’re in New York, California, somewhere with high SALT taxes, Florida we don’t see it as much, but basically what happened was the cap got increased from $10,000 to potentially $40,000. But it starts phasing out pretty quickly, so high income earners are phasing out and going back to that $10,000. There are a lot of tricks with pass-through entity tax elections on the business side to get around it.
[04:44] I still think at the end of the day, investors are just looking for where the most profitable places are, and the places with the highest SALT taxes right now are just not the most profitable. There’s other things too, like rent control, a lot more going on there. So at the state level, it really comes back to whether that state is going to be real estate and investor friendly, and what the profits look like in that area. Even in Florida, what’s happening in Miami is completely different from what’s happening in Jacksonville. I’m not seeing as much impact in Florida, but there’s a bit of relief for people in higher state tax areas.
[05:30] Faith: I know, I’ve been seeing the shift go from Miami to Boca to Delray, now Boynton. It’s slowly making its way up the state, real estate is definitely growing quicker here than a lot of people realize, which is exciting for investors too.
[05:56] Daniel: It is. If you’re down in South Florida, if you’ve been to Miami, there’s only so much room, it’s already packed to the Everglades and to the beaches. So you can only go up vertically or start expanding into other areas.
[06:10] Faith: Yeah, absolutely. Where do you see owners missing proactive planning opportunities?
[06:15] Daniel: What I think a lot of owners are missing is they think there’s going to be some exotic opportunity out there they’ve never heard of. Most misses are just common, basic planning, but it takes time, you need to know what’s going on and coming down the pipe. People get over glorified thinking there’s some random IRS tax code that’s going to save them a bunch of money, and that’s not really how it is. There are a bunch of tools in the tool bag, and you need to understand what these strategies do and how they affect your situation.
[06:45] A lot of times it’s about asking, what are you doing with yours? All these tax strategies and savings, they’re not saving you money just because the government wants you to pay less taxes, there’s a reason. What’s the reason, what are they trying to get at? That’s something that matches with what you’re trying to do. A lot of times people are missing out because they’re expecting some grand thing where they come in and immediately save a bunch of taxes.
[07:26] It’s often not sexy at all. It’s more about planning out years in advance. As simple as, this year you’re going to have a very low tax year, so we push a lot of things off into the future when you’re going to have a much higher tax rate. Just playing with tax rates, going from a 20% rate to a 37% rate, that 17% difference, purely by playing with timing, has saved people millions of dollars.
[08:13] Faith: Wow. How can tax strategy reduce overall risk, not just liability?
[08:18] Daniel: When people think taxes, they just think tax liability, how much am I going to pay, how can I make that lower? But you have to think about it from a lot of different angles. One is audit risk. It’s very expensive to get audited, very time consuming, it can last many years. So you want to make sure you’re lowering your audit risk, which comes from understanding what the IRS is looking at. You might not be intentionally trying to do anything to get audited, but if you’re working with an experienced preparer, we know exactly what a tax return should look like, what should be reported, and what the red flags are so you don’t accidentally get flagged.
[08:56] And when you do get audited, they start looking at everything. It’s also a legal risk. There’s a lot of different risks here, so you want to make sure you’re properly doing your tax returns, keeping proper records, clean books, depreciation schedules, how you’re recording everything. All of this affects your overall tax liability and gets overlooked.
[09:20] Bookkeeping, great bookkeeping is the biggest difference between people saving a lot of taxes and people paying a lot of taxes without knowing it, because they don’t know how much they’re saving. Here’s an example. Say I go to the store and want to buy something, they sell it to me for $100, but it’s 25% off, so I’m only paying $75. I got a good deal, saved $25. I go to a different store, they’re selling the same item for $75, no discount. I got the same value, but I think I got more at the first store because of the discount. That’s normal human thinking. A lot of times with bookkeeping, you don’t realize how much money you’re saving by overlooking it, because you never knew you were saving it in the first place.
[10:03] Faith: How many messes have you had to clean up?
[10:12] Daniel: Bookkeeping is always terrible to clean up. When we have clean books, the tax return goes well, you actually save more money on tax liability, tax preparation fees, less risk around audits and legal stuff. Even if you get sued for a legal purpose, having clean books makes everything smoother and easier. Messy books feel like you’re saving a dollar today for potentially spending a lot more money down the road.
[10:44] Faith: Absolutely. What should owners be doing mid-year to stay ahead?
[10:50] Daniel: Mid-year is actually prime tax planning season. Tax season is when everyone, CPAs and clients, are worried about getting tax returns done. Mid-year is usually the best combination of last year being done, so you can fully focus on this year, and you have enough time to actually do something, because a lot of tax strategies take time to implement.
[11:17] You want to analyze your business or whatever you’re doing. If I want real estate professional status, I need to truly understand what that means for tax purposes. Do I have the hours, do I have the logs? A lot of times I see people say, I’ve heard about real estate professional status, I bought a rental property, let’s take it. And I have to step back and ask, did you actually do any of this? Some of it may be eligible, some isn’t, and they’re usually falling short. I have to be the one to tell them, you’re too late, you’re not going to be able to take it this year.
[12:04] So then we push it off, and next year we really understand what you need to do. Buying one or two rental properties might not be enough to get real estate professional status, you might need more if that’s really what you want to do, but you need to understand the time and lifestyle commitment. It’s not a one-time thing, it’s every year making sure you’re getting your proper eligible hours in.
[12:37] Faith: Yeah, and I think about 80% of what’s on TikTok is made by AI, and you could be listening to and following an expert CPA in real estate who isn’t even real. Working with a real person like Daniel will save you in the long run.
[13:05] Daniel: Anything on social media is a mixed bag. There’s actually good advice, you just don’t know when you’re getting good advice and when you’re getting bad advice. That’s the biggest problem, it’s hard to decipher what’s real. So you have to fact-check everything if you don’t know it or it’s complicated. I usually recommend, if you hear anything on social media, check it with your CPA before you do anything.
[13:47] Faith: 100%. Okay, so last question, what’s one move real estate owners should make before year-end?
[13:57] Daniel: The biggest thing is to actually analyze all your properties. This is the time to do it. Before year-end, look at every property and ask, would I buy this property today if I could start over? Is this property doing well, is it cash flowing, is it getting the return I want? You have a half a year to start doing that, and real estate really is a long game, so when you’re looking at your properties, you should map everything out.
[14:41] The best investors have an exit strategy before they’ve ever purchased a property. They understand how they’re going to buy it, operate it, and exit it. Life throws wrenches at you and you have to change things as you go, but that’s okay, as long as you have a plan and you’re assessing your properties every year. That’s when you can start really digging into tax strategies with your CPA, bonus depreciation, cost segregation, 1031 exchanges, or even more complicated things like the historic rehabilitation tax credit if that fits what you’re doing.
[15:29] You start getting into whether the complexity fits what you’re doing and whether the cost savings are worth it. I always tell clients, return on investment is great, but sometimes return on hassle is even better. We all want to save money, but do we really want to do a bunch of activity to save $5? Truly understand what your return is, not just on investment but on hassle too, to see if it fits your strategy and your lifestyle.
[16:08] Faith: I love that, solid advice. Well, it was so great to talk to you today, Daniel. Thanks for everything, we’ll have you back on May 28th.
[16:20] Daniel: Yes, May 28th, I look forward to talking to you again.
[16:24] Faith: Looking forward to it. Thank you.
Ready to Build a Year-Round Tax Strategy?
Waiting until tax season to think about strategy usually means the best opportunities have already passed. If you own investment real estate, talk with a James Moore professional about a plan that works year-round, not just in April. To hear the full conversation, including how SALT limitations are affecting investors and what to review before year-end, watch the complete episode above.
All content provided in this article is for informational purposes only. Matters discussed in this article are subject to change. For up-to-date information on this subject please contact a James Moore professional. James Moore will not be held responsible for any claim, loss, damage or inconvenience caused as a result of any information within these pages or any information accessed through this site.
