Even if I outsource the labor, I still find myself spend too much time doing the design, shopping for materials, and managing the schedule of several sub-contractors (removing current tenants is another pain in the neck, both time-wise and emotion-wise).

In terms of a negotiation, I just asked open ended questions directed towards the pain points so they would make a mental image of why they want to get rid of the property without me.

Showing the house with tenants is a pain because of logistics of scheduling.

I grew up in Erie so I know your pain.

Welcome @Harry StandaferI feel your pain about professionals not living up to my expectations which leads me to do everything myself which frankly is just stupid on my part. 

In addition to the FCF, the monthly principal reduction is $300.Property 2: Every month the property requires a cash infusion of $200.

high 4% rate, 5-7 year fixed, recourse2) Agency (Freddie/Fannie, CMBS, life co):  Pain in the butt to get, but low 4%s, 10 year fixed, NON recourse(Edit:  I live in commercial multifamily world.  

I just feel like I'm throwing money out of the window (at this point, with a new work balance) and it pains me to pay someone monthly who's providing me a service that's being handled extremely poorly. 

Moving is a pain, they're not going to break their lease and haul out all their junk just because you *might* be selling.The flip side is if the current tenant really likes the house, they may consider buying it.

There are an additional 10+ steps in the process when compared to a vanilla FHA Loan, and those steps can be painful, prolonged and expensive if you don't get a lender that can really lead you in the right direction.