Unfortunately local politics often lead to policy considerations that are intended to drum up voter base appeasement as opposed to doing what's best for the municipality/city. 

I’ve heard having solid policies in place is key to rentals by the room.

I know for certain there are professional PM's that stopped listing on VRBO a few years back when they changed their policies, but I don't know those PM's well enough to get the relevant data.My first inclination was "I need 5% or more increase in occupancy to make it worthwhile".

I recommend focusing on getting a great investment property and disregarding Section 8 in that pursuit because any property can be a Section 8 property, but a lousy investment is lousy regardless of having a Section 8 tenant or not.Section 8 will perform a basic functional and safety inspection for your units after you have an agreement with a Section 8 tenant and your local housing authority.

I have been able to find companies that will cover real estate portfolios on one policy in other markets but no luck in the Florida market.

Your primary insurance policy with $300,000 in liability coverage should be sufficient in 99.999% of all lawsuits.5.

Your primary insurance policy with $300,000 in liability coverage should be sufficient in 99.999% of all lawsuits.5.

This is covered under Regulation X (1024.5(b)), outlined here: https://www.consumerfinance.gov/rules-policy/regulations/102...

Apparently it didn’t go on auto renew like the other policies and paperless means I never got a dang notice of cancellation.

For example, wood rot is not covered in most policies.