I would not be doing long term financing on section 8 nor would I own any.. just my personal goals.

Many investors who are in a similar position in my market (another HCOL/tenant friendly area) choose 1 of 3 options.1.

When someone who is not an electrician wants to do electrical work and you choose that because it's cheaper, don't you already know the answer?

But I also realize many people choose the direction of Appreciation first.In my hometown market (not Pittsburgh, but central NJ area), few small to mid size multi family properties could come close to cash flowing positively.

It all comes down to you researching and aligning with the area that you feel will fit your investment goals best. 

It's a balance of cashflow and wealth accumulation.One of the goals is to have tenants pay as much of your cost-of-ownership as possible (loans, taxes, insurance, etc.)In high-cost areas, any Class A or B property you buy will usually negative cashflow for the first 3-5 years, until rents rise enough to cover the negative cashflow + rising taxes & insurance.Investing OOS increases your risks because you may not know the market and you can't check on everything/everyone all the time.If you move forward with your buddies, HIGHLY recommend creating a solid Partnership Agreement!

My goal of course, is financial independence as soon as possible. 

I choose that market due to affordability, potential cashflow and cash on cash return. 

The goal of the first 3 deals will be to target 1-4unit styled homes, requiring minor-rehab.

The goal is to achieve and maintain financial freedom.