Scaling-  your question is both country and even town specific.  

This specific deal was a close friend's apartment that he was renting.

@Tanya Maslach "I came away with several neighborhoods in Ohio"Ohio is on my radar for MTR, specifically rural areas in Columbus/Akron/Cleveland. 

- we are aware of the statutory requirements, just deciding whether the tax benefits would be worth it to us for the long term for a specific property - 

Hey @Mike Nelson, never assume anything about STR rules and regs.Here is the STR rules for Oak Park - https://codelibrary.amlegal.com/codes/oakparkil/latest/oakpa...I would call the city and make sure it is legal for a specific property.Now regarding the famous person angle, sure it can add value to the property or as a STR, but for STR use, I would think you would need it to be in original condition with a lot of the furniture and knick-knacks that were owned by the famous person along with a bunch of photos etc featuring the famous person.If you buy a place that has been totally redone but was owned by someone famous but has no features or things that were theirs, then I don't see it being a draw. 

Also, if your unit was not previously listed within the year at a specific rate, you may definitely be able to list your unit at what the market is currently.

For a yearly lease agreement specific to Phoenix, AZ, you might consider starting with the Arizona Association of REALTORS® (AAR) or another local real estate organization.

You can find both and you can reduce the commission but you may need to do more work.More specific on your questions about price, that is also negotiable.

One workaround could be keeping a separate spreadsheet to track your adjusted tax basis accurately and only using Stessa for operational insights.You could also reach out to a cpa and see if they have a specific recommendation for software to use.  

I have had two amazing mentors in very specific niches, but they retired.