;)I generally prefer to have architects (rather than engineers) prepare drawings that need to be submitted to building departments because they are more up to date with building codes and other language that usually needs to be on the drawing set. 

We are thinking of buying a small condo in the Destin, FL or Gulf Shores, AL area... we prefer Destin.

Note... we have a very low nightly rate, due to not being beach adjacent and not being in the best part of town (though I feel we've made the best of that in various ways), and because our "business model" leans towards a high volume preference. 

(I would be looking in recreational/2nd home type locations for land that already had water, sewer/septic, power...preferably).

She has another tenant wanting to apply and prefers the condo furnished compared to the the first approved tenant who prefers the condo unfurnished.  

I prefer to use OPR (Other People’s Money) and we all make money in the end.

@Blake Lawrence, the tools will adjust your price up/down according to demand, special events and etc... but ultimately your base rate is what sets the tool.I used Wheelhouse & Beyond Pricing at the same time,  setting the same base rate( i have 2 houses on the same st that are the same size and rent for about the same ) , there was no notable difference on how their pricing adjustments worked, I did notice that Beyond Pricing was a little more aggressive raising and lower rates, but that can easily be replicated on wheelhouse if it is a strategy you want to follow.Beyond Pricing has the advantage of being the preferred Homeaway partner.Good luck

However, as I am currently locked into an apartment lease for the next year, I might look to buy and rent out.Looking to local investors for their preferences and thoughts!

Preferably someone you can vouch for by personal use, not just a friend!

A drive-to vacation, where the biggest expense is the STR rental, is going to be preferred by many.