Banks are regulated by the government, while owners are not regulated.

Also, with more government regulation,  man-made canals and new docks extending into tidal waters are becoming a harder thing to find. 

A lot of these southern beach & mountain towns have been supporting STR for 75+ years, long before Airbnb was a thing, so they’re very comfortable with it and it’s a built-in part of the community.A lot of Northern places are FREAKING OUT over STRs & STR regulations & they don’t seem to be very supportive of it.

If everyone doing wholesale deals operated as intelligently and with as much integrity as you we would have no need for a regulated real estate market.

OR is it the State of CO and FL that are wrong...or other states that are regulating the practice?

It is always difficult to start some new activity, but you have to do small steps to your goal - make savings, find a responsible real estate broker, get familiarized to all regulations and rules of successful investment strategy, so just prepare to face numerous difficulties, especially with regard to your situation.

Laws change, HOA regulations that can hinder your ability to run this business.   

Since the assets are held by their irrevocable trust, instead of the client / recipient, the government does not count those assets for qualification purposes. 

And also the opposite when I sell a used work vehicle I sell it usually to a worker or subcontractor and I hold the note and he/she pays me kind of like private buy here pay here As long as I don't break the regulations for the DMV about how many vehicles can be sold per year I'm OK

Have you studied your state landlord tenant regulations.