I figured its a win win, they get to invest into some real-estate and grow their retirement as well as it will lighten my investment and potentially allow me to get into a better property that would cash flow/appreciate better.Does anyone have personal experiences or opinions on this?

Your first thought, without gimmicks is great, but will you have the cash to buy any of the properties because that is always the first gimmick of wholesalers?

Do not focus on cash flow first in Philly or you will end up in a C-/D+.You HAVE to work with an agent who has been in Philly for a long time to have success and who owns properties there.

If you have a $1,500 or more spread between cash flow and living expenses, I would consider saving the rest to add to a cushion. 

Purchase price: $140K% Down: 25% (I am considering pitching the investment to a friend and making this a cash purchase - any advice regarding this decision is much appreciated!)

Might be a good way to get your foot in the door, not having to partner with anyone, low downpayment and a cash flowing asset. 

You should win an award with most thorough and easy-to-understand response Jonathan. 

Ideally, my property generates around $500 per month cash flow after accounting for rent, insurance, tax, interest, PM fees.I’ve recently realized that repairs costs have notably affected my profits.

I was thinking about different ways to avoid the 6 month period in which one has to own the property for in order to refinance cash out.

You can get great cash-flow in Cincinnati and I think C areas would be your best bet.