I've worked with several investors out of more expensive markets - CA, NY, etc - who find our prices much more attainable than buying in their own backyard and so therefore, I'd say your exit strategy would include getting your FOR SALE properties in front of out of town buyers.

Then 10 years into it, my cash flow was up to $30K/year, including covering several thousand a year in small nuisance repairs.

My insurance broker, Sobie Insurance, has several companies that provide insurance coverage for Airbnb rentals. 

Can anyone advise as to the health of the rental market(s), as well as recommend a great investor-knowledgeable realtor?  

Please DM me. i know several active maritimes investors.

Thank you & Blessings for Health & Prosperity !

This is important because if you want to look in several states but are working with someone that isn't licensed in every state you would want to plan ahead of time to have several agents that could give you the coverage needed.

The current plan is to go straight into a rental, then begin the process of home buying (primary residence) within a month or two of getting settled, knowing it could take several months to find what we're looking for. 

Additionally I like to evaluate the financial health, capital reserves, and property condition of the association to try to understand whether a large assessment is looming.  

@Jeff Stansberry Jacksonville has several small multi families but they rarely stay on the open market.