Everything is a balance of risk and rewardMost importantly in my view: Do you have discipline to follow rules that you have learned about and accept long term?

Your financial discipline is your investment foundation.

That's a disaster waiting to happen unless you have proven yourself financially disciplined for a long time.

Some properties need all disciplines, occasionally one does not need an area fixed, or so I am hoping...It would be much easier to hire a general contractor and just pay the bills, but have not found 'that' person here that I trust to have my interest in mind and who knows how to keep the ball rolling. 

If you have been able to save $100,000 cash and as you mentioned you max out your TSP every year you are extremely disciplined in regards to spending and saving, so again great on your there.

I am looking forward to my real estate career, but education is also an example of hard work and discipline.

It also doesn't take into account your personal financial self discipline.

I recommend you save up $10,000 so you can show the lender that you have discipline to achieve a financial goal, even if you lack real estate experience. 

If you're disciplined to save the amount you were spending renting or on a more expensive mortgage, you can use all of those saved funds to to it again in a year. 

First thing first, learn about Discipline.