I'm curious if underwriters have any algorithms or programs that take care of this automatically based on a few inputs or if they largely pull comps manually? 

The programs we have are called the "Way Finder" & the "What If Simulator".

DTI will be your biggest issue in qualifying though, granted much more lenient on DTI (usually up to 50%) than an investment loan (usually under 40%).Last idea - give thought to downpayment assistance programs.

If you are having a cash issue, you should also ask your lender how much of a seller concession is allowed with their loan program.

If you have to graduate in 2 years, that means either a full-time program, which probably isn't reasonable, or an EMBA.

@Dan Schweit I'll throw out a totally off the wall option as well: taking advantage of iBuyer programs.

I am looking into revitalization/jumpstart programs in Maryland.

The only thing I didn't do is spend the 25k+ on mentor programs that I thought was stupid because the info was already out there. 

There are also hard money programs that care less about credit and more about the deal, have you tried that route yet?

There is a fee for this as a percentage of your commission, but I think there are at least two choices of programs so I'm not exactly sure what it entails at this time.