She originally wanted 8k to atleast cover the cost of the roof but I told her that I can’t pay that with the state the house is in.

Basically, if you can re-rent a unit for enough more monthly to cover a mortgage in the amount of the improvement then you should do it. e.g. if you can get $100+/mo in rent... that's worth spending roughly $15k in remodeling costs which will then be covered by the add'l rent.

I also suggest you buy an Umbrella policy covering lawsuit.

So i am covered. :-)

The DMV area is a big area to cover, so I would recommend you picking a general location to start learning about. 

That covers pretty much everything from the studs up including the markup on labor / materials.

Further, I think you're saying the original owner also signed a modification raising the 1st mortgage balance without any notice to you, adding $25,000 to the cost you'll have to cover to obtain the home yourself in foreclosure? 

The NOI (Net operating income) needs to be sufficient to cover the payment and some amount of spread.To make the numbers simple lets pretend the payment on the 50K mortgage is $500/month and the 70K mortgage is 700/month (these are likely high numbers) if the rents minus expenses (excluding mortgage) net out to 750 then the 70K mortgage is pretty risky since there is only a $50 spread and the 50K mortgage is much less risky with a $250K spread. if these numbers held up I wouldnt buy the property at all unless I could get a 60K mortgage with a 600/month payment and have a spread of $150 and 10K in cash reserves. 

I think everyone covered what could’ve been said but I wanted to correct you on your statement regarding beginners luck to emphasize that it was far from that.

If you have it already included in your analysis then you are covered.