The idea of eventually owning multiple properties that produce a steady cash flow is extremely appealing, however, I understand that I have A LOT to learn. 

I think if you run the numbers on the deal above with financing you will see that the return is actually pretty attractive.

Vacant homes are frequently broken in to and attract squatters and unsavory characters.

It is a decent income producer. 

She bought a great house which she likes and the property is producing every dime it is suppose too.   

Starting to focus on Ithaca, NY (plenty of grad school renters) and Indianapolis (I'm there at least once a month for work and it seems like a growing city) but open to any and all areas that produce stable cash flow properties. 

I get 10 a month at a minimum.And if I gave you my secret ( well I won't) but there are ways to attract more sophisticated sellers and I have never seen it discussed on BP or even remotely thought of.. but its worked for me for many many years.. so I think I will just keep that pearl to myself.

Also when comparing maybe a prospective buyers own market to some of the more popular TK markets, the price are more attractive. 

I feel it's a trade off worth making if you can locate more attractive deals.  

The other thing I didn't agree with is that if I'm forcing my potential buyer to produce a Cashier's check, I'm making them jump through an extra/unnecessary hoop.