The goal/strategy is to find properties in the Philly area that could be rented out and generate cash flow. 

Monthly Income: 1100Expenses:•-Repairs/ Maintenance – 50•-Real Estate Taxes – 112.50 (1.2%)•-Insurance – 30•-Vacancy Costs – 83•-Capital Expenditures – 100•-Total Monthly Expenses: 375.83 Downpayment: 18000Loan Amount: 72000 (with 20,000 rehab money)•-30 Years @ 5% interest Closing Costs: 4000Total Initial Investment: 22000Monthly Mortgage: 386.51Cap Rate: 9.54%Monthly Cash Flow: 329.32ROI: 17.96%After evaluating this, if this property was in a better neighborhood with less crime, would I be naive to pursue this property?

I was looking at Dover/Portsmouth for a small one family but am a bit lost in terms of what to look for and what property in NH would generate the most income.

For some, that money they gave you initially, was all they gave you.

Is there any legal issue I would run into if I only kept scanned copies of leases electronically, or better yet, only had completely electronically generated and signed documents like real estate agents use?  

To answer your initial question-- no, I'm not seeing that happening. 

As you can see I have some initial upfront costs (higher monthly budget) but then it decreases.

The initial numbers worked, so I put in an offer, got it under contract, and got a contractor out there to get an actual bid on it. 

It can generate rents of a thousand monthly approximately.

I feel this strategy will work best for me since I can continue to recycle my initial working capital over and over again which will allow me to scale quicker.The end goal is to have a large cash flowing portfolio which I'm prepared to work full-time at to ensure that I succeed.