I feel like a condo would allow me to: 1) Get experience and my foot in the door with little capital.2) Protect me from getting wiped out by an unknown capex expense.3) Potentially house hack.4) Not feel bad about burning money on rent. 

This FLA build new rentals got WAAAY over sold and huge FOMO that got buyers to lose their wits about how to protect their money..

There are ways to mitigate the costs and protect yourself to the extent possible.

I probably won't withdraw it, so the long-term tax savings and asset protections are appealing.Anything I am misunderstanding or not considering?

A well written management contract should clearly spell out what is expected of both the PMC and the owner, to PROTECT both and avoid misunderstandings.

And I wonder if CCR or HOA can restrict these to protect the values of those homes ? 

., property management companies aren’t legally required to carry general liability insurance, but it’s highly recommended for protection against bodily injury or property damage claims.

When starting out in wholesaling real estate, it's important to use agreements that protect all parties involved while ensuring a smooth transaction process.

As long as we keep any of the protected classes out of the discussion, is it ok?

I used Protection One when I was there.