(gambling if you will).

In part, split urban areas like Philly take a lot of gambling in regards to safety concerns and appreciation.The urban gentrification bandwagon is something that tempts so many of us east coast folks.

However since she hasn't figured out how to save yet might not be worth the gamble.

Without the background education "gambling" is a better term than "play" although they both amount to the same thing.

So you're gambling on the future, and in the meantime you're a landlord (although obviously you have experience with that).You could do some rehab, but the problem with putting lipstick on a pig (if you'll pardon the crude expression) is that you have a good chance of picking the wrong shade lipstick.  

Provided you aren't providing fraudulent paperwork, there is no rule against 'helping' an appraiser do her or his job well and see the value that you see.

I too think planning any deal with conservative numbers is the best move--unless you NEED 12-15% CAP rate--but then we might be gambling and not investing ;-).

You might be able to at least see in the property if you cannot buy it from the owner.I love to gamble, but there are people at my local auctions that have no problem spending $5,000 to $750,000+ on homes they have never seen.

You will be hard pressed to find people willing to gamble on you without a solid track record.  

But also return on investment is better.A gamble for a newbie, but can be a way to learn the business.And go for the smaller properties.