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. 

. 🎢 Market trends, investing methods, and economic situations are like a rollercoaster—they constantly change and twist.

FICO is 780+ and currently have 4 other investment properties including 2 STRs in the same market we are trying to close on in West Virginia.

Just wondering can you ever catch a great deal on the market  and if so what’s stopping you from taking advantage?

Insurance is a lot trickier and somewhat state specific.  

., if real estate is held outside an IRA, heirs inherit at fair market value with zero built-in gain, eliminating capital gains tax.

I also have no interest in being in the car wash business, or the laundry business, or the AirBnB business, things like that which seem to appeal to a good number of people, but not me.I like to KISS, and just focus on market rate rentals, 12 to 18 month leases.

Or you could decide that you're going to hang in there for family/legacy reasons, and keep raising the rent whenever the market supports... and whenever you turn over a set of tenants.

Most lenders in this market are less likely to issue a loan that you will default on.

Purchase price: $150,000 Cash invested: $15,000 Sale price: $301,000 Found this deal off market and flipped it quickly for a profit.