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".

However, there is no clear instruction on how and where to apply for it.

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.

Instruct the tenant than that because she has threatened a lawsuit your insurance company now requires ALL communication regarding THIS issue to now travel through your lawyer at _____@ legalplace .com and that she can continue to use your online form provided for other non-emergency maintenance requests.

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.

If you ever forget to include this in the contract, ask your escrow officer to include it in the escrow instructions.

I am looking into revitalization/jumpstart programs in Maryland.

They will have instructions on rental properties.