I'm just sort of feeling like I'm spending too much time/mental energy dealing with folks who don't stand a chance.

Based on these numbers you would pay boot (taxes) on the 10K that wasn't used for the loans but in reality with appraisals closing costs fees you will probably spend the 10K  If not pay the small tax or increase your down payment on one property.You get the pictureBottom line is work backwards or at least from your next step.  

My brother is about to head to college and I was thinking about perhaps putting a down payment on a triplex were he could live, after showing my parents the money he will spend on rent during his 4 years ( about 14400$ since rent around the university is about 300$) they have decided they could pay half the down payment (10k) if I instead don't charge him to live there.

Since my goal was both equity and cash flow and I was new to this I instantly jumped into the Equity portion rather than letting the effects of the rehab on the property and financing build equity over time and this has hindered my growth in number of properties because I spent way too much Capital per $1 of cash flow.So, how much capital did I spend per dollar of cash flow to get a single dollar of cash flow?

I'm pretty sure you can rent it (if 5% conventional) and apply for another loan as primary for 5% down again.The process may be longer than if you get conventinal loan with 20% down but you are spending less money in down payment.I'm thinking of the doing the same.

Which doesn't really make sense to me since all NYC properties are +500k .. you'd think someone spending that much would do their homework before hand.

I spend 21.6k + 4k + 8.5k = 34k for a property valued at 66k (50% discount).

Spending most of my time on the books, at the age of 14, I understood that creating wealth has nothing to do with hard working but more with financial education.

I am interested in the BRRR strategy as well since we don't have much cash to invest (don't want to spend our emergency fund).

While I live in MD, I'm about 90 min away from Baltimore so I don't spend a lot of time there.