Given your stated position of things, assumptions of skills and network, I'd say your best path is a totally different one. 

I have multiple listings across different parts of Florida and I don't even live in FL.

Whether it’s sprucing up a property with a few renovations or doing a full-scale flip, a good contractor can make all the difference.

I'm considering investing in STR in Hawaii to diversify my investment portfolio (mainly for capital appreciation) as well as it being a regular vacation place for my family.

You can always hire a different PM company.

The suburbs are each very different with some having no restrictions and some completely outlawing them.

It is the same as an umbrella when it comes to liability coverage and covers you if anything happens but the difference is it only covers the property while umbrella covers auto and property.

Yes, its mainly ordinary income from interest payments.

The delay in the foreclosure may mean a few different things.

It can be used to monitor markets, filter results based on lots of different criteria & even includes annual revenue numbers that you can work backwards to see how certain markets/properties are performing.