We also have some mobile home parks that we are selling and we have some luxury short term rentals.

And if anyone knows has experience with Rise Capital Group or Sunrise (now offering mobile home park/parking lots).

See below screenshots/map area.I did a similar strategy when bought a 4 unit in Rogers Park to help myself create high cashflow. 

Typically  issues are raised when the exterior is not kept up with / parking on grass / garbage in neighborhoods where everyone takes pretty good care of their homes.If you keep it clean and run a tight ship, you should be okay most of the time.

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.