Cost up front was made clear about 10K.  

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. 

@Nick RichardsI agree with most of what you had to said and gas prices will effect my budget.

Has anyone found a more cost-effective alternative that can match CoStar?

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.

Also, keep in mind factors beyond the down payment, like closing costs, potential renovation expenses, and the need for property management.

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?

That gives me additional income and offsets the risk of loss if I have a longer vacancy once they leave. 25% sounds like a lot, but consider what it will cost them to find another rental in the next 30 days that will allow a three-month lease, plus the cost of moving, setting up utilities, etc.There's nothing wrong with trying to help out a good tenant, but don't hurt yourself in the process.

My opinion for those that live in a high cost of living market is to continue living / renting in that market and invest in a different market that is affordable and provides both cash-flow and appreciation potential.The reason to stay in the HCOL market is because you will be paid(hopefully) a nice large salary.You can take this salary to then 'easily' invest in other markets.NYC is tenant friendly which can be a con for investors.Furthermore, NYC has appreciated historically.