I earlier suggested a guarantor with deep pockets primarily because the situation sounds non-typical, and from a bank's perspective "high risk" so having a wealthy guarantor they can go after would help to mitigate some of that risk for them.

Wind Mitigation and 4 Points within two years are just a new requirement for these carriers.

The property is in FEMA Shaded X flood zone and on high ground but surrounded by wetlands/swamp far from any main bodies of water.I'd like to hire someone to look at the property and tell me if the wetlands are going to help mitigate, or make worse, future flooding events.

Another twist to mitigate would be to build one of your homes specifically to use as a model home. 

I’ve work in “water mitigation” field for over a year.

So I asked if we could start looking for a possible tenant to help mitigate those options in my favor. 

It definitely can be mitigated if the other half of your investments in the diversified dividend ETF is doing decently well.

have them put a radon mitigation system in the home.

The tree situation wouldn't keep me from purchasing the house if the deal was good enough to cover mitigation.

You get the most favorable financing, your down payment is much lower than a rental, you can therefore afford a more desirable asset which mitigates risk (nicer properties appreciate more, are easier to sell, attract quality tenants and have lower vacancy/turnover), you will learn the ropes without nearly as much risk as an OOS property presents.