They have high loan amounts and a very long draw period and long pay back period.

I am very data driven and I simply don't see Philly as an attractive destination unless you are -- local, hands on, DIY, don't have prop mgmt expenses, don't pay leasing commissions, get preferred rates from lenders, know a guy who does handyman work, etc. 

Pay attention.STEP 1:Lists, foreclosures, absentee owners, probates bla bla bla, you need to send thousands of mailers calls or texts to get one deal yes?

transacting - buying and selling - is expensive and can consume years of gains, with all of the commissions and fees you have to pay. 

Many lenders offer competitive introductory rates, so if the goal is to pay off ASAP you will benefit from this. 

Now you need to figure out how to find deals and pay for them.

I pay an accountant well to make sure I have as little profit as possible :)For a small operation Google Sheets could work. 

The issue I run into, based on what I can put down, is that I would most likely have to split the mortgage down the middle (I pay half/Tenant pays half) based on current rental rates and current mortgage rates (considering what I can put down).

If that is the case, you sell the house, pay off the HELOC, and use the $15-$20,000 to get into a new house.  

DIY will be the "cheapest" - you can set up an account on the MA DOR website, register your LLC, you pay over the whopping $500 MA charges you to register an LLC, and voila, you are off to the races.