Having a good mentor to help you navigate will influence the level of difficulty and how you maneuver so I think it’s highly important.

I am finally ready to get out of analysis paralysis and get some skin in the game!

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. 

For example, I'm not too sure about how to actually find good deals/distressed properties, and how to actually find appropriate property managers, CPAs, lawyers, etc.I think once I get started and inertia starts to build up, things will make more sense, but it's that first step that I'm finding difficult.  I

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.  

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

This concerns me as the investor appears to have very little skin in the game.

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.