If you have need of help or suggestions on anything my background is working for the 219th RED HORSE squadron as a Structures troop for 10 years, in civilian contracting for carpentry and concrete refinishing, as well as property management just to name a few things.

I used to try and lead horses to the trough in the beginning.

I stayed on a horse ranch in Winchester last time I went to the wineries in Temecula.

$2k vs a purchase of a new(used) truck is nothing. unless it's brand new, that new(used) truck that you're getting could breakdown when you're rolling it off the lot, and, unless, the dealer gives you some sort of warranty, you could be stuck with an even bigger headache. i would never purchase a vehicle for cash (unless it's cheap). debt is super cheap for well-qualified people these days. you can make far and beyond the returns vs the interest you'll be paying on your note. i say fix the old horse and make that money you have work for you. edit: evan and other folks mentioned writing the truck off, so that is definitely something you'd want to look into. i totally overlooked that above. this could sway me into recommending the upgrade. i'd still fix the old horse :)

I'm not sure where you are personally or financially, but you might be putting the cart before the horse- it will help us give you some direction if we know what you plan to do once you get a bite. 

Would love to hear other's stories if they have gone through this to help get me back up on the horse.  

This is the most cart before the horse post I've ever read.

The Tampa/St Pete market is kind of unique in that you can have a ghetto type of neighborhood, next to apartment building, single family, horse ranch, crack house, and a $1million house all within a mile of each other!

So if you're looking to "refinance" your recently acquired rental, and use that money to buy the next one, hold your horses.  

Hold the carrot in front of the horse, but pay religiously when due.