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. 

---You can try to increase your chances of cashflow by buying a beatup property and BRRRing it.2) Buy Class C cautiously.

The Retainer Fee is credited towards whatever they buy from us in the 90 days, so in effect, costs them nothing.Note: we're not doing this to make money, but to avoid the time-wasters.

This only really matters if you plan to buy a house again soon...within 9-12 months4.

You should just buy in Georgia...that’s it!

You could convert them to a DSCR loan but then transfer them to a LLCWhat we have done is save for down payments and renovation costs, - buy properties that need work rehab them and then refinance them out making sure it meets our dti.

Search for and buy a bad roof.

If you really hustle and are smarter than the average bear, you may make enough money that you can buy an investment property.

He'll still be renting - just from you instead of others, and at all the costs to you that you have enumerated.Your son doesn't "need" to buy a house.  

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.