In these situations, we generally give them the option to sign a month-to-month agreement with a huge increase or have them sign a lease for the whole year.

That is the cost of doing business and the risk you have to calculate. 

I'm not sure if this is possible, but maybe the listing agent can do it and you increase your closings to pay them back. 

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. 

The shorter the prepayment term has an impact on increasing the rate.4.

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.

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?

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.

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

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