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.

If you routinely try to get the next tenant in so quickly after the last tenant, perhaps you can add a penalty to your lease for holdover tenants.

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. 

If cash flow is your goal, you might look into areas like Jonesboro, Forest Park, Lithonia, or Stone Mountain, where RTP ratios tend to be higher these are just a few areas I'd suggest.

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. 

Close proximity to NYC, the nearby state park, and a destination by itself for certain people.

They are not allowed in certain master planned communities.Summerlin, including Sun City Summerlin▪ Town Center▪ Skye Canyon▪ Cliff’s Edge▪ Symphony Park▪ Grand Canyon Village▪ Las Vegas Medical District▪ Providence SquareAnd these restrictions I find would be the most difficult for you to overcome - A short-term rental license does not provide authority to violate any common-interest community’s covenants,conditions and restrictions (CC&Rs).