with many supposedly 'cheap' houses in the midwest is that they are OLD and have lots of deferred maintenance that is not obvious from a visual inspection. 

It is a very nice building and no, I did not consider skipping insurance, although I suppose I could have, it is paid off. 

I suspect that bridge is supposed to have railings on it much like a porch would if it is more than 18" in height.

I suppose just finding a handy person who's willing to take calls, or be "on call" from tenants, maybe for an additional "on call" fee, and a decent cleaner.

Apparently, I am supposed to choose a sponsor but am having trouble sifting through the plethora of options.

Interesting, but since we use a PMS it is irrelevant for us I suppose. 

I suppose I could find something out there for less that needs more work but I’m afraid anything much less than 200k in or near Tampa area is a total tear-down kind of job, which I don’t want to do from across the country for my first investment.

.: @Kevin G.I suppose the issue is who is looking for what... and what risks are you looking to take.Nothing is wrong with you doing the GC "function" of getting the trades in and out, etc. 

When it snows cars are not supposed  to be left on the street, but pulled off onto the lot or a parking deck.Know the ice/snow load. 

So I suppose the main point is that to just make sure the addition/ADU is "legal" when it comes to zoning.Hope this helps!