I am concerned with the major output for repairs but does that matter?

Sometimes, you need all the time you have available to address any issues or concerns.

The fha 100 mile rule will be triggered whenever you try to vacate your current primary and also trying to use the rental income to qualify.However, this 100 mile rule can be exempted for the following rulesRelocationIncrease in family sizeVacating a joint owned propertyNon-occupying co-borrowerIf you are not trying to use FHA on your 2nd house hack, you can use conventional and the rules that I mentioned above will not be a concern and will be exempted.

By last night and early this morning, I did suggest that they evacuate but that they could stay if they didn't have any other options (surge is my main concern, we are on the 18th floor so I don't think they will have an issue with that and we have Miami/Dade qualified hurricane protection)...BUT, I was very forthright that they would likely be without water and electricity and stuck on the 18th floor possible for some time.  

What’s your biggest question or concern about diving into the market here?

Equity/appreciation is less of a concern for me, although it'd be a nice to have. 

The major concerns to me are the roof, the hot water heater, and similar.  

A strong labor market can lead to wage growth, which further fuels inflationary concerns, making the Fed less inclined to cut rates in the near term.However, many recent jobs reports have been revised downward after their initial release.

Less desirable and by no means luxurious but not dangerous, no intensive management needed, properties unlikely to appreciate much over time but very attractive from a cash flow perspective.

When I see this, it's concerning because.. why are so many decent looking homes in a "warm" market temperature on the market for two plus months???