I primarily/ultimately want to get into multi-family complexes and am unsure as to whether I should aim for some (section 8) SFH in Baltimore City to build up my capital/equity.

Aggressively paying down the mortgage by supplementing the 500$ in cash flow with an additional $1,000 in personal income we would pay the mortgage of in approx. 10 years and save more than 120K in interest payments.

So looking at the numbers: ~$10,000 out now to finance first deal, or effectively buy a new furnace soon & eventually aim to hit $110-$125/mo cash flow after that.

I’m not sure if that was aimed at me but if so thanks @Ryan Mullin

Long term, I would like to just keep buying and holding, I would like my W2 job to be a supplemental income with my real focus being in real estate, and if I do decide to quit my job, that will hopefully be a realistic option on the table. 

I am not sure how much I should aim to have before I even start thinking about searching for a house or what price range I should be looking for?

I’ve thought about RE agent, or trying to find an entry level job in mortgage lending, or even workIng for someone doing rehabs and/or buy & hold would be awesome as this is what I aim to do as an investor myself.

All of the numbers I was using were "lender estimates" which I understand generally aim for erring higher rather than lower.

If so how much do you guys aim for since you can't purchase value add type properties the VA loan?

Purchase price plus rehab is aimed to cost no more than 70-75% of ARV (based on sold comps)."