Your situation is different than the majority of people on the boards and the general population; you have a paycheck for life. 

Seems like it would be a good place for economic development.Cool city, with great prices and really not all that far the the "Big" Cities.Probably has a good workforce of hard working people.How do you feel like your economic development board is?   

Next, I would find out who the attorney(s) is in your area that is known for regularly dealing with the Zoning Board.

Well....should you invest in a city where the people elected a woman with foreclosures, liens, judgements, garnishments, ethical violations from the state ethics board,  misused a city credit card, went three years arrears on her federal taxes all while yelling for other people to pay "  their fair share, " left skeletonized dead bodies hanging over Canal St for months on end covered only by a tarp until the wind blew it off to reveal to our horror her blatant disrespect for human dignity?

Part of the reason I threw myself into work and used to work 60-80 hours per week until I was let go last year when a new Upper Management came on board and started replacing managers with personnel from his previous employer.

A novice going out of state to start is an absolute recipe for an unmitigated disaster -- just look at the out-of-state threads on this board.

If you're near a medical and/or law school, monthly rentals are preferred by those who are preparing for board exams over vacation rentals as well as by visiting professors. 

"Income Charge- This charge may only be levied by the Board in accordance with the Community Authority Declaration.

No and you need to put this on hold and research the condo nuke that's about to hit Florida in the form of new legislation that no longer allows condo boards to defer necessary repairs. 

I assure that is the conversation in those board rooms "ah, almost feel sorry for the suckers, but hey, business is business".