The was a guy there who controlled 80 units! 

I have just put together several properties in and around Baltimore with a former Real Estate Devoloper Partner that has control of these properties.

Any time the Lender is in control, a Short Sale is possible; once, twice, ...

It was her grandmother's house before her parents moved into it in the early 70's.  

As a wholesaler you should know what to do and how fast you need to do it.Here are some suggestions:Write an offer for what she wants.Take title subject to the mortgage, keep the property, pay the mortgage and profit from the rent and appreciation -- orControl the property with a "skinny contract of sale" with a delayed settlement date, have a public auction.If you control the property for $65,000 and sell it at $80,000 you are doing well (need a partner).I'd say stop asking question and go close that deal.May I ask you some questions?

I live in Baltimore County, Glen Arm, and have done transactions in Columbia and a ton of them in the County and a couple of tons of them in the city as a family business, controlling and selling houses and commercial properties.

I'm looking to control my downside as much as possible here.

I think my parents place is the better option.. that equity is hard to pass up.  

My brother is about to head to college and I was thinking about perhaps putting a down payment on a triplex were he could live, after showing my parents the money he will spend on rent during his 4 years ( about 14400$ since rent around the university is about 300$) they have decided they could pay half the down payment (10k) if I instead don't charge him to live there.

Risk management and controlled leverage will become your best friends in this business.Keep learning from the posts here on BP and don't forget to seek advice before your next deal.