Work with a tax professional (preferably a CPA that does tax planning and not someone at H&R Block or TurboTax) to ensure you qualify.

I'm surprised someone verbally told you you can convert back to a duplex and didn't tell you that you must get permits.from what you are describing it seems the town gave you a hard time because you didn't get permits, I don't know that you have any legal standing to go after the town,  again, I am not an attorney 

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. 

This for us is preferred over seller financed deals as we can do 65% LTV, 800 credit with someone who has net work 2x+ loan and get double digit rates. 3.

Consider:1. investing time in finding a local landlord mentor--someone whose been doing it for years.

There's no reason to provide details, though I do let people know if anyone asks that we do not accept bulk up-front rent payments or anything like that because I absolutely do not want a prospective tenant to think that someone else swooped in with a bunch of cash last minute.

I have succesfully done this on IGMS PMS software.I would also make sure your email is listed on their VRBO account. you will then be able to get inquiries and messages on your email account so you know when someone messages.

Is there a customer service phone number that I could use to contact someone at BP? 

My area is relatively low crime, but had one place that someone broke a window to get in.... probably a homeless guy looking for a place to sleep....got scared when neighbor turned light on.I put in a SimpliSafe unit... portable, easy to set up, multiple options- you can use a webcam and get alerts on your phone and future tenant can pay for full service if they want. 

You’re likely to see someone want to control the rehab portion as a way to secure their investment.