However, I feel like there's a lot of potential to run into a lot of walls/pitfalls that can cost a ton of time/money if I do this route.At the end of the day, I want to put a lot of emphasis on using the newest technologies to streamline the business as much as possible. 

Unfortunately, the cost to get into the real estate game down in Florida is just way too much for a first timer in my position.

It's tougher to get cash flow upon move out these days but if you're patient, willing to do some work, or live in lower cost/fringe areas you can make it happen or at minimum put a serious dent in your housing expense which is still a win in my opinion compared to renting or buying just a primary home.Also if you're a bit short on cash, make getting a seller credit part of your financing strategy.

Coming up with half the cost or maybe if you have two partners 1/3 of the cost is a lot easier than all of it.This all sounds great, right?

For what it is worth I had a client cost seg their AirBnB in Gaitlinburg and it reduced their taxes owed by 26K. 

The better option is for the Seller to pay your closing costs.

I have new builds sitting because the windows or floor trusses are taking longer than originally estimated.

When you do repair cost do you do minimal repairs or upgrades?

Also, the length that the investment is held impacts the settlement cost.

Depending on how big this unit is, I would probably bite the bullet and pay for the relocation, then add a washer/dryer and raise the rent by some amount to cover the cost.