At the end of 2023 I purchased an old 4plex out of state (MD) for $180k (it appraised for this amount), 20% down with 7.99% rate, mortgage is $1364 with piti.

I keep getting mixed answers I don't know why this real estate professional tax status is confusing to me along with cost segregation and bonus depreciation no matter how much I read about them Do you pay a good tax professional to give you an answer?

Emphasize how this arrangement could work to their benefit, offering steady income, avoiding a traditional sale process, and giving them the freedom to move forward with their plans such as buying that sailboat and sailing around the world.If they ultimately decide they’re not interested in selling, you’re still in a great position to continue your search and buy your own property in the near future.

@Shiloh Lundahl,At this point, the amount of time you're putting into this is making me laugh. 

Wishing you all the best as you take this journey.

And here's a tip...When you think you are all done; stay in your new STR for 24-48 hours and keep a list of each thing that you were reaching for that wasn't there. 

There are surely STR Facebook groups for this location.

This is typically for most people not a DIY project. 

Truthfully horrified that this is an individual who wants to raise capital from others "to scale" after owning section 8 rentals for 2 years.

Just a different takeNow this is not to sayPS - those houses that were priced way too high and languish?