Near by there is the Woodbury Heights apartments, and I spoke with someone from the zoning department last week that mentioned those apartments were helped out by the city for development before selling them.

ARV back in March when I bought it was around $245,000 but the market's appreciated a ton since then and there's some comps nearby that support as high as $275,000.

I'm willing to travel to Tampa or near by area if necessary to learn/help if needed.

If you can't purchase a property near by that works for your strategy (flip, rental, BRRRR, etc.) what makes you think going OOS will be any easier? 

How much is it worth to make an out of state mistake versus a local mistake that nearby friends and family can jump into a car and go help correct?  

I estimated that it would appraise for around $140k-$150k now based on the values of nearby houses.

You are right, I’m concerned about the appraiser looking at comps for a generic office space (which would bring in less revenue) compared to other nearby buildings with short term rentals.

I checked nearby houses of similar lot sizes/beds/baths and they have a current home value of around $300k.

He tried a couple of times over the years and could never get approved for a traditional mortgage, so he just started stockpiling his cash. 

Most companies will use an automated program to base their appraisal value on, which will likely be lower than what you think your home is worth, or what nearby comps are.