I personally would sell unless i was fairly certain that some significant appreciation would be on the horizon.

I just talked to him this morning and he said they're not making sales calls into FLA today with Hurricane Irma looming on the horizon.  

Check with First Horizon... they have programs to refinance one day on title using the appraised value, even some HELOC programs to .pull cash out.

What time horizon do you guys use to determine the value of the upgrade...i.e. if I spent $15,000 but was able to push the rent up $500, then I could recoup my costs in 2.5 years and assuming I didn't have to do any more upgrades for the next 10 years, I would pull in an extra $45,000 in rent over that time.  

I'm just trying to expand my horizons by updating out of state folks on what I am doing and hopefully creating more funding in the process.

Craig when you run the numbers you plan the "time horizon".

"Buy and hold" might require a long term investment horizon: 10-15 years (unless you are starting with 550-600k).I think if someone was really motivated, they could join a RE management company right after college to learn the biz.

That's a good point about the time horizon.

https://seekingalpha.com/article/4240746-concerns-real-estate-market-stock-market-whole  Another buying opportunity on the horizon? 

I would caution against simply seeing cheap pricing and assuming the area will appreciate within your investment horizon, unless you have reasons to believe it will happen.