I’d also reach out to the Hancock County Planning Department to get a feel for how flexible they might be on replating and rezoning—better to get ahead early.For renovations, if you don’t have boots on the ground yet, ask for referrals through local investor-friendly agents.

Totally emotional questions but I tend to feel that paying off a primary residence earlier is better because you never know what the future holds for you and your income. 

My wife and I tend to look for Commercial buildings with a residential component to them.

There are plenty of ways around an HOA but they tend to break the rules that you committed to following.

The numbers in the long run tend to be significant.  

i think you are wrong, but it doesnt really matter. and in my market, VRBO tends to be the bigger booking platform

Union City I tend to avoid, there are a few pockets that work for MTR but for the most part the city's rental laws make life very tough for landlords. 

Unfortunately, I tend to agree that they really are not concerned with whether or not you have to cancel bookings. 

Any thoughts, suggestions, or referrals on what first step to take are appreciated. 

I think that equity gains in good areas tend to outstrip the value of cash flow in the long term but if you're pumping money into a rental property you're going to need a hell of a lot of equity to make up for not only the additional funds you put into it, but the opportunity costs lost in that money and the money that's in the property.