Good luck continuing into those deals in your market and thank you for your service! 

In more astute owner/property manager interactions, the contractor will be TOLD to decrease their price ASAP or the contractor would be terminated for any future consideration.I would most definitely contact the contractor to get the low down as to why it is more, since the property manager won't do it.It sounds like since you are doing a la carte service as opposed to full service, you are getting some bad answers from the property manager. 

Assuming all rents are substantial they should be able to cover my debt service and any other expenses needed (repairs, water, vacancy, cap Ex, etc.) 

Are you also providing pool service so it will not be a green pool? 

So here's the story. My wife and I have finally started in on our REI journey and bought a second home. We will be moving into our new home (Oct 1st) that will be Owner Occupied for 6 months as we do repairs, updates,...

I have a couple that I plan to use Tax Title Services for, so I am already familiar with their services but I plan to keep those. 

In a emergency, I could be up there in 2 ½ hours.Taking into account comps from other rentals on VRBO & AirBnB, services fees, VT room tax, cleaning and management costs, I think my break-even would be in the 60-80 nights/year range.

Nic DeKramer No test purchase yet, but Wayfair Business Services claims to beat any similar/exact product.

The key is the trains that service norther NJ, The commenters.

Most SFR home inspectors will perform the same service for multi-unit properties with an additional cost per unit or square foot or similar.