We were thinking of trying to own a STR property, but again given the difficulty in meeting requirements, it doesn't seem likely to be beneficial at all. 

First, if I understand correctly, you considered conveying the property to an LLC but because of having to pay doc stamps you're considering conveying to a trust but you are having difficulty finding insurance if you do that. 

Tenant flip costs go up due to more difficulty terminating bad tenants.  

Find something you really enjoy doing and look forward to.my specific advice is to get up earlier and do the workout then, at least if you start running into difficulties finding the time.

Difficulty Selling Properties to Free Market again, NOT correct. most investors want sec 8 tenants in.

One of my property managers does not post a PDF copy of the lease with the tenant on my owner portal.  When I get a new tenant and ask for a copy of the lease they resist.  As the owner, isn't it my right to receive a...

@Christian Orellana any major metro in Florida is going to present difficulties in cash flow for the first few years.

However, it must be the current boom in home renovations and the opportunities for bigger fish to fry, as I'm having difficulty finding someone responsive.

A thorough understanding of legal concepts, contracts, property rights, and regulatory difficulties may be gained via studying law, especially real estate law.

Difficulty Selling Properties to Free Market again, NOT correct. most investors want sec 8 tenants in.