Not to mention the costs of setting up and maintaining multiple LLCs in Delaware or whatever safe harbor to get you real liability protection.

The last owner of my property did weird stuff like pout rainbow floodlights in the basement. these are big and get pretty hot fast so i bet they're very costly to run. im going to replace those with energy efficient LED lights. i figure if i can optimize where utilities are wasted and keep the bills down then rent will be on time.

The effects of a collection a long-reaching in this way, so your best bet is to get this fixed ASAP and you be the one who initiates the contact. 

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.  

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.

As this is my first deal and I want everything to be smooth as possible, I added an additional $50K to be safe. 

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.

There is an IRS safe harbor for this practice extrapolated from Rev Proc 2008-16.If the property is his primary residence then as mentioned above he can take advantage of the primary residence exclusion. 

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.