Its unfortunate that your closing costs increased by $3,546 in order to fund your tax and insurance escrow accounts.

He can also refi down the road to lower his interest rate... but that comes at a fairly significant cost (say $3,000 - $5,000) - which will totally negate any mortgage pay down from owning the property in the first couple of years.  

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.

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

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.