Again like driving your car, laws can be state specific, and it good to check with a local title company (that is investor friendly) and possibly a real estate attorney (to make sure you fulfill any disclosure requirements). 

These steps don't fulfill Asset Protection, but its a step in the right direction.  

I would fulfill my one year obligation of living in the property then I would move out and rent out all three dwellings, using a mixture of Long/mid/ and short term renting.

(currently reading through all of Brandon Turners books) Couple that with not finding fulfillment at my 9-5 for the last year...I am interested in any advice/tips or stories anyone has to share on this topic!

After fulfilling the commitment, started renting it with 30+% cashflow.

Could talk to a lender for sure but it's hard to get a second FHA, there are certain requirements you must fulfill. 

It does take a leap of faith that is done with the backing of solid analysis and knowledgeable members on your team to fulfill tasks you're either uncomfortable overseeing (like acquisitions, bookkeeping, etc) OR who can be consulted just for advice. 

Similarly, GC's can't fulfill the designer's role simply because they are executors (not creatives) that get the job done for a given budget.

Plus I’d fulfill my dream of living by a beach for as long as I please.Any recommendations?

ALL HOA rules are different so definitely check to see what your specific HOA's says.Best case scenario would seem they protect everything and you can get a bare bones policy which fulfills the umbrella requirement.Let me know if you have any additional questions!