But we were all working full-time then, and we decided that rehabbing and doing the mailing (and responding to calls) just wasn't feasible.  

Currently in school, and put together a feasibility study for a property in Chicago.

Short sale seems like the only feasible solution to getting out of the property.

The available cash does not include a modest emergency fund or retirement accounts.From some research, it appears I may have these options:- Hard Money Lender (or Private Money Lender)- Construction to permanent loan (not sure on DIY feasibility)- Conventional loan for house, then separate renovation loan or hard money loan just for renovations- FHA/government backed renovation loan (possibly just include "contractor" work in this with minimum down payment and then DIY  the rest with remaining cash)

While there isn't a "minimum" loan about, you're pretty close to what is actually feasible.

I see some FHA loans with 55%dti, but are those feasible with low 5% down payment? 

Would 100K be enough money to feasibly leverage that request?

Structuring a deal with a private investor will not only be more flixible and cost effective, but also feasible.  

Second what @Dan K. points out about inspections, especially when you can't throw more cash at the down payment/purchase price to compete.Keep an eye on Chelsea, Everett, Malden, West Roxbury, Roslindale, Roxbury, and the Grove Hall side of Dorchester - there are still multis that haven't been converted to condos, all (to varying degrees) on transit and feasible with some patience.

I'll give a few a call and see if anything is feasible.