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. 

I'm eager to learn more about:Identifying undervalued properties: Are there any specific strategies or resources you recommend for finding deals below market value?

I had specifically asked for numbers including mortgage payments and they emailed to me.

I'm not sure what specific areas in OH I'll focus on yet.

Quote from @Joshua Janus: Cleveland, Ohio is a great market to focus on for cash flow and specific pockets have gone up 2x and upwards of 4x in the last 5-10 years even!

I recommend honing in on one specific strategy to get started and then go from there.

It essentially includes having a buyer for a specific property BEFORE entering  in a contract with a seller.  

However I ran a few quotes on Obie Insurance (geared specifically towards landlords) and for only the 4 houses I checked, I am saving 1,5k a year if I switch.

There are state specific items to take into consideration.

Each CPA will answer the questions uniquely based on their interpretation of the tax law as well as your specific scenario, so I highly recommend having a trusted CPA answer this for you.