Even without a budget for repairs/etc - let's just define "cashflow" as income left over after PITI & utilities for a moment - Mac Groveland and Highland Park are going to be tough.

Larger families, remote workers, or investors could see it as ideal, especially if local schools or amenities like parks, dining, or entertainment are strong.

6) What parking requirements/issues will you run into?

At the time I looked, 20 or so years ago, the problem with smaller down towns is the proliferation of nearby strip malls, where the stores are surrounded by a large parking lots, and for laundromats, attract more customers as they can park easily, walk to adjacent stores for shopping, snacks, and browse newspaper and magazine racks, which explains why they do better, there's more customers.

What's your take on purchasing cottages in RV parks for rentals?

We had a paved area for parking where we built the ADU.

How is off street parking.

My preference is Single Family, although I currently own some mobile homes, some parks, and some small multi-family as well as notes on land and houses. 

Keep knocking it out of the park, I look forward to seeing where you go.

For example I have a 4 unit in Rogers Park chicago its gone from working class with some gangs to now houses over a million being built and rents up 50% to a few years ago, same happening in Portage Park and Albany Park.