So I think JLL is the main brokerage I should be hoping to work for, but I'm not sure how long JLL will be in this seat with VA. 

You could easily get 75-80% LTC on the cabin build meaning you'd need about $200,000-$250,000 CASH, to complete the project.Take 200k out of the FL house, build, rent, refi & payoff the FL property again would be my best bet about going about it.

My point is that the extra cash flow is easily spent on improving the properties and thereby increasing the value. 

I could very easily rent the property again but my plan was to sell it and use that cash for the next investment.  

You will need to factor in rehab costs, which could easily eat up another $50-75k depending on the condition.

A lot of issues are much easier and more inexpensive to resolve if you can easily go to the property.

I can easily get us personally another “vetted” 20mm.  

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.

I feel like they play by more subtle or more aggressive rules that I don't understand quite as easily as simpler markets like Denver and even places like San Francisco.

Is there any way to easily find out what areas around detroit are what class?