A month post closing, the son of the buyer (mother) has written a "legal" request to have us buy him a new refrigerator.  

Investment Info:Single-family residence buy & hold investment.

Publication 15, Employer's Tax Guide, says only this much:...Payments for the services of a child under age 18 who works for their parent in a trade or business aren't subject to social security andMedicare taxes...No definition, and IRS publications are not really law anyway.

I originally wanted to buy into a vacation rental market but this last year has been crazy and we seemed to have been priced out.  

Who's gonna buy them?

Unless you've done substantial improvements to the building or used a large down payment when buying, it's unlikely this will work.Perhaps your best move is to find a new primary residence that is 2-4 units and repeat the process.

Going through my real estate journey I have learned a lot, I am 24, a veteran and a graduate from Temple University,I started with aspirations of investing on a property and making a quick flip.My problem lied with fear of failing, my capital and my savings.I decided I wanted to learn the real estate market and know the ins and outs before I would make a bold choice on buying my first real estate home.

Then bought my own deal the following year 37.7k sq ft warehouse on 4 acres in Plano.Been buying industrial for last 6 years.I think your plan is right, I'm a big proponent of joint venturing on commercial deals.

The hang up is getting deals formally drawn up.One idea:- I buy the property and pay 25% DP, then they provide capital after the closing and I pay them P&I over 5-10 years.

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.