@Demetrius Cooper Best advice for such a short time frame, I'd open a checking account that provides a high yield.

Our cash-on-cash return would be much less, but we'll still get principal paydown and everything besides the roof should allow us to raise rents (central air, updated appliances, open up the kitchen/livingroom wall, refinish wood floors).

In this case, getting it notarized might be a good idea.You might see if the new contractor would be open to deferring some payments until the property sells. 

@Larry Fried I'm open to both as long as the numbers make sense.

Now that I've been enlightened with BP, I've now been more open to the idea of "managed" risks. 

To "learn the market," we went to 10 open houses since early-to-mid February.

We've generally had to pay the maintenance out of pocket over the years - an AC compressor, garage door opener, new dishwasher, paint/carpet etc., but spaced out and we had money in savings for those. 

Short version of long story: multiple arrests quickly followed.The process likely varies by jurisdiction, so learn what options are open to you where you live.

Asking a renter to deal with such an issue opens a huge can of worms.

Since he is a friend of yours he might be open to letting you rent with some sort of credit towards buying the place in a year or two.