Trust me, issues will come up.

Destin has some larger vacation homes, but in my humble opinion the prices are already toward top levels. 

Rental income: I learned to trust MLS listing agent "ACTUAL RENT" if this is available on the MLS listing.

The report of the apt, as neat and clean and moderate smell of smoke does not rise to the level of damages IMHO, and even considered legal notification.

Credit/debt isn't really a huge issue, it's more our comfort level.

Besides that though, I believe there is a finish level that can separate your units apart.  

All of the factors you decide on determine what you will be drawn towards.Person to person, we all have different levels of risk aversion, time, etc. and that is going to determine a lot of things for you.

So I think my best strategy is to sell myself and my vision, but be willing to pay until I feel comfortable that I've learned enough to start trusting my own estimates.

You are totally right though, even though I feel that I am cautious I just can't have the same level of caution and fear that others who lived through 08 have.

I have owned the property in a trust since May of last year, and recently transferred the property to my name in November.