House flipping is a lot more straight forward, land flipping can get complicated and depends heavily on what's going on in the surrounding area + how you market it 

Also, some want detailed info and registration of your LTR tenant and for the homeowners association to approve them prior to placement.2) If you are looking at the Tampa urban core, SFR appreciation heavily beats condo/ townhome appreciation over the last 5 years.

In some areas, heavily Section 8 neighborhoods have higher crime, high maintenance costs, and lower rents.

If one tenants property is damaged as a result of the negligence of another tenant, if someone is injured while visiting one of your tenants or if someone is injured driving home after drinking heavily in one of your tenants units and sues a renters policy will likely respond respond. 

I am looking to invest long distance and so far have been relying heavily on internet research for neighborhood data.

If the property doesn't cash flow (i.e. cover your mortgage payment, insurance, HOA, PM cost, other expenses) then I'd say it probably doesn't make sense to hold long term unless you're expecting that area to appreciate heavily in the future (i.e. future development, etc), especially since you mentioned you're moving back to the Midwest and should be able to find better cash flowing rental properties there.

In markets where they're known for STRs like at the beach, homes are sold furnished but not heavily marketed that way because of what is considered "real estate" legally. 

And this is by operating in a heavily pro tenant environment. we are mostly focused on buy/hold in core locations.

That would be considered a lease option (heavily restricted in Texas).If they ask for written documentation of the $75000 price in 2 years, you will have to tell them that they have to trust your word and remind them that you have $5000 reasons to hold up your end of the deal.

I was also disappointed that they included so many locations that were heavily regulated.