I have a guy on my team that is successfully renting by the room to young professionals, travel nurses, and college students, but that is downtown Indy. 

I am confident there are many parts to this I do not yet comprehend.

Safeco, Travelers, Foremost and others. 

Water does go through the cracks and water will travels to the walls and down into the subfloor.

Not even sure where you are pulling 30% from...Taking money from a traditional retirement account(non-Roth) now or later is subject to income tax at your marginal income tax bracket.Any 'planning' around distributions that you can do later can also be done now.If you want to take money out in a year where you are in a lower tax bracket(result of going back to school, taking a year off from work to travel, a year where you have a lot of losses from real estate via Real Estate Professional Status, etc).Also, hard to say what your income / tax rates will be when you retire.

Our experience in renovating and selling homes, coupled with our individual professional backgrounds, gives us confidence in our ability to succeed in this new endeavor.

There is an abundance of supply, high price tag, it's more of a corporate travel town than a vacation destination (meaning that 1-2 bedroom units are in most demand, which puts you squarely in competition with hotels). 

Currently in Lancaster County but travel for the right projects. 

I'd refinish them if you have a quality contractor who is confident they will turn out well.

I travel a lot so I listen to a lot of audio books.