Human psychology is a fascinating thing!

Why would people use CONtractors that cause them pain?

It will definitely be grind at first with lots of growing pains, but if you can get to the other side it is worth it.

If parking is scant or ill-defined it is bound to be a pain-point for your tenants (and you) and something that fuels their turnover more than is good.

Five of the units have fuse boxes.They can all use a paint job.I imagine a lot of the rehab work would be a pain with tenants in place, so I could just rehab as they go vacant, but then at which point should I refinance? 

I've been trying to use the BP Rental Calculator to find a property on the MLS that would generate a modest monthly positive cash flow and it has become painfully obvious that I am not going to be able to get there using that math on the available small multifamilies where I live.

Make sure you put the Phrase "Signed Under Pains and Penalties of Perjury".

You are seeing an example of it right now...and probably don't realize it...yet.You said you have all your properties paid off (I'm in pain right now). 

Detach yourself from the emotional/psychological hurtle and trust the numbers Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

The IRS is a pain with these 1031's sometimes.