1) Get your contractor/electrician/plumber to see what you HAVE to do to remain within code requirements and meet those at a minimum.

Quote from @Quincy Jones: I am also looking in Milwaukee, had a real estate agent literally give me a drawn out map of the areas color coded to show the different others that are the best to the worst, I’d start looking in areas that are starting to or in the process of being gentrified.  

They were installed to code and are oversized for the square footage. 

If you're interested let me know I can get you a 1 year free trial code. 

With the evolving code from planning and city council I'd like to know if it made it easier for your project.

. -- Greg, does Facebook still post your video ads in your area only now that you can't choose zip codes?

I'd definitely recommend visiting the city's planning and code department.

Get 3 contractors to give you an estimate on bringing it up to code/ rentable condition.3.

As has been discussed ad nauseum, you will want to make sure code allows a short-term rental wherever you are buying.

Turns out, I believe the Cleveland Heights code doesn't allow you to have "sleeping rooms" in the basement.