If your goal is to learn to raise capital Joel Block's Dealmaking Symposium is great content and well worth the investment.If your goal is to learn to do financial analysis college courses may be your best bet.  

Anyone have a preference on one versus the other, and why?

What, if anything, is their curb appeal versus yours. 

Equity investors are willing to take that risk in exchange for higher rates of return, i.e. 14-18% versus the bank’s 3.75% for the “safe” portion of the capital stack.

Local Bank will be your best bet; though my Refi took sometime... they didnt ping me too bad and when i told them i wanted the Refi to pay off debt...that helped alot and they cut the checks for my bills.

However, I have not found a duplex that has had any positive cashflow after renting both units with the quick rule of thumb and was wondering if my best bet would be to buy something in in hopes of breaking even/ paying a little every month, but relying on the equity build, appreciation, and tax benefits.

Is the acquisition cost the same for oceanfront vacation rental versus college rental townhouse? 

I bet there's not a Landlord on here that would donate $5,000 to help her pay rent, even though that's exactly what they will suggest you do.It's OK to charge someone what something is worth.

I bet you are stuck with what you have.

Versus taking out less money and therefore having less money on hand in exchange for some cash flow each month but not have the cash in hand.I strive to have my RE at 70% to 80% LTV.