You cant strictly be a PM in most states if you dont have a RE license but Im not sure if managing family property is an exception.

Perhaps I'm too strict - but that's a topic for another day. 

If I purchase too high, I'll have to bring my own money into the deal to cover the difference, which I can do but I can't believe the seller is being strict about list price.One mention was that the seller had $24k of assessments they would have to pay at closing, and that was a reason why $27k just wasn't going to cut it.

Someone in a protected class may not qualify but if you exclude the strictly for being in that class you get in trouble, the city which issues your license in Philly views different classes as protected.

@Aaron Phillips, maybe ask for your (refundable - but with strict non-swoop conditions) Assignment Fee UPFRONT? 

Would I still survive jumping into this new adventure even with a strict moving schedule for the next couple years, or would it be recommended that I hold off until our residence is a little more stable? 

If you are strictly looking to fix and flip, or hold and rent (and not to live in yourself), check out Bergen Lafayette.

This combined with a strict tenant screening process could yield a very high quality tenant, because as you can see most landlords restrict pets for the potential damage and liabilities they have experienced or hypothesized.  

I honestly didn't think a whole lot about the appreciation of the homes, it would make sense if the houses were purchased for way less than what they are worth now.I've ran some numbers and I think it could work if I got a place in the area, but from strictly an investment standpoint it looks like there are quite a few better options in the general Baltimore area.

Terms for your first deal include 12% interest rate and 4 points, they are willing to negotiate future deals but are pretty strict on the first one.