They'll also want to know if you can handle the carrying costs like interest, electric, water, sewer, garbage, house insurance covering construction, etc, etc, while you're doing the renovation.

More important is your ability to carry this property assuming it's 100% vacant.

Know your market, figure out what utilities owner carries, what repairs/capEx are needed, etc, what did similar buildings sell for?

There is obviously less "risk" with just paying off my loans, but I am not afraid to carry my student debt if I am confident that my money is being better used elsewhere.Thanks for any insight and opinions! 

(Many gentryfyimg parts of DC are well beyond 2006 levels)Higher income areas with concentrations of wealth tend to carry less risk while lower and middle income areas carry more risk for significant drops in property values.

but a lot goes into analyzing a deal, including: $/SF, Average Days on Market in the area, how easy or difficult it is to get permits in the area, how long the flip would take, comps/ARV, Rehab, Rental Rates, how the area is trending, holding/carrying/hard money costs, closing/commission costs etc.If you can analyze the deal, you can then negotiate the deal with sellers, buyers, and lenders.

Purchase a property which the seller owns free and clear and convince the seller to carry back a loan2.

Cash and carry.

I do direct mail to Mom and Pops and the people who respond are usually over 65 and looking to retire...and interested in carrying seller financing. 

Everyone else has left the business because they are sick of the city riding them constantly for everything and the insane bonding they are required to carry.