Hi all — hope everyone has squared up with Uncle Sam. I’ve got a mindset question for the group: I run one short-term rental, now in its third full year. On an operating basis, 2025 was unprofitable for a variety of reasons. That said, I’ve since dialed in revenue and feel confident it will be consistently cash flow positive in 2026. Here’s where I’m wrestling: I completed a cost segregation study that generated meaningful tax savings in 2025. When I factor that in, my after-tax result (NOPAT) was actually quite positive in year two. In fact, the tax benefit was strong enough that even with projected operating improvements in 2026, I expect to be roughly flat to slightly up in NOPAT year-over-year even with double-digit revenue growth. So the question is — should I be reframing how I think about 2025? I didn’t get into this business for the tax benefits alone, and I don’t want the tax tail wagging the investment dog. Should I consider 2025 a “profitable” year, or is that just mental accounting that masks the underlying performance? Curious how others here think about this.

Hi all, I'm a long time user of Quicken for my personal finance. I know, you can make fun of me - I get it! At any rate, it worked perfectly fine to run my part-time rental, part-time 2nd home through their Business & Personal software option. However, I'm a full-time real estate investor now, closing on my 2nd property next month, and am considering leveling up! With 1, soon-to-be 2 properties, and dreams of 2-3 more in the next 2-3 years, please answer my poll, I'd love to hear your POV as well as any commentary about why you recommend what you do. Could be from a tax / CPA perspective / real estate investor perspective / or small business owner perspective - I'd love to hear your thoughts! Thanks in advance, Josh

What pre-work activities for a specific deal prior to closing count towards your material participation hours? Also, is there a tool you would recommend to track that?

Hi all, I'd heard that filing an extension can be beneficial, or at least common practice, for Real Estate Investors. Can anybody explain the rationale for doing so along with any requirements to do so? Thanks in advance, April 15 is around the corner!