@Julie Doke: Industry specific software speaks to you and you can easily relate it to your day to day process.

While podcasts, books, seminars, and websites offer general knowledge, you'll buy a specific property in a specific location, subject to local rules and regulations.

I also use their virtual credit cards which enables me to assign a card to a specific person, like the cleaner for my STR for example, so when she runs a charge, it automatically drops into the right account in terms of categorizing my expenses.

However, I agree with you that I will never again work with that specific attorney again.

Hey @Anthony Sigala many folks might be optimistic about this rule but the "rule" was created during a very specific and particular time in real estate as a way to help newer investors have a framework on how to approach rental properties without going in blind.

@Ashish AcharyaYou're merely reproducing the IRS position, the one I specifically challenged.

That said, I highly recommend speaking with a local professional in the DFW area to get insights tailored to your specific goals.

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

I've specifically learned a lot from Dave and Henry on their podcast, but also appreciate Jesse Vasquez' approach with her mid-term rental investments.

These were not specifically related to owning rental properties but the clients' assets (including any owned property) was better protected due to having umbrella coverage.