David I have not sold real estate at the street level in oh 20 years..

Midtown and Brickell in Miami are the hot spots for the city. 

In Hawaii the debris was systemically removed, wrapped in plastic and disposed at a 70+ acre site the city acquired.

We are looking to buy a condo in Chicago as the new rental, for a variety of reasons, but most importantly because it would rent better in the city, and it fits our desired price point (so we can allow for the rest of $$ from the sale for paying off their Oregon home and pay all, or some of the taxes on the boot). 

If a mortgage has a deed restriction, not allowing short-term rentals that is not imposed by an hoa or a city government how hard is it to get it removed?

I retired 10 years in and my wife 14 years into the journey. 85 % of my portfolio is 200 year old converted city row homes that are maintenance monsters and we still have enough cash flow to retire from our W-2.

(Wisconsin, Indiana, Ohio, Michigian).Pick a more rural town/city, they are typically very safe.

I believe I misstated the TX city earlier.

I'm looking into cities of central AR (LR, NLR, Benton/Bryant) Hot Springs area, and NW AR (Fayetteville, Rogers, Bentonville).If you don't mind me asking, what is it you like to offer new investors?

I generally recommend if you're not going to buy a property in the city/market where you currently live, the next best place to look is where you have family (and presumably a place that you'll visit relatively often and easily).What is your price point and are you looking for turn-key properties or something along the lines of a "fixer upper", assuming you buy in Peoria or a similar priced Midwest market?