Even a tree falling on the property or fire would not be covered, if they found out you "broke" the policy agreement by using a landlord policy for a STR. 

If you're going the umbrella insurance route, perhaps see if it will cover you for several things including just the routine slip and fall (like mold or earthquake).

In Florida, this situation falls under our Unlawful Detainer statute.

I use a scoring system where applicants gain and lose points and their total either meets or falls short of my established line in the sand.

All the HVACs in the units above us have their drainage such that the water falls on our unit.

A degree is something not only to fall back on, but also gives you skills.

It may fall off a little for 3+ years. 

Your area falls in our target market as well.

I am looking for ideas from experienced BRRRR folks on how they would handle such a situation with a tight budget, especially with fall approaching and SOD going dormant.

Those are two bear traps that investors fall into daily that will absolutely demolish you and put such a bad taste in your mouth you may never return.Nobody wants to pay 3 points at 13% on a bridge loan, but if #1 and #2 above go well it will never kill you.