It increases cost and creates time pressure that he would not have from a straight sale.

I can barely get firms to look at columbus with 10x years of experience thats mostly for ground up. the average house cost is still less than 100k which means you have a lot of houses to tear down still to create a housing shortage. the economics don't make it favorable for any type of investing but turn key or maybe ground up in the urban core which works in any city. but compare any of these cities, I'll take Indianapolis, Chicago, Minneapolis, and columbus and Milwaukee and pass on the rest. 

Even in the smaller markets, a life cycle of a deal can stretch out 6 months before the exit and that can cost 30k once all is said and done.I like to tell people 50k is a nice starting point capital wise. 

Some people purchase a property for cost segregation/accelerated depreciation purposes to save on their taxes.

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.  

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

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.