Where you pick will depend on your goals for cash flow and your budget to buy.

So depending on what your investment goals are and what type of properties (Class A through C/D) and where in the city you want to buy, that can directly impact the level of stability one can find within the market here. 

I currently live in WA state and invest out of state for buy and holds.

I am a long-term investor with a buy and hold property in Brooklyn, NY and I also own multiple lands in Florida and Mississippi.

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. 

Can you find a way to capitalize on their work even if you don't buy "their deal".

They will see a large pipeline of local deals, and they will buy some as rentals, flip others, and flip the contract (wholesale) a handful where it makes sense.

To get a rough ballpark, sure, but sometimes you'll be way, way off like we've seen with the iBuyers who it turns out were too smart for their own good and ended up buying high and selling low due to to relying on data and not actual organic, boots on the ground experience pulling accurate comps like an appraiser or realtor who knows the market on not just a block by block or street by street but a house by house level.

@Jay Hinrichs my thoughts exactly, I feel they are big enough to email blast crappy deals and know someone out of 100,000 will buy it.