Also was hoping to get some recommendations for investment-focused real estate agents that cover Morris County and Essex County.

You have to gauge what the market will be willing to pay for.Some things that you didn't mention... the roof looks rough in the front.

If the landlord's already owed $500 from the security (say 2 months into a 12 month lease), that may not leave much more security to cover all future damages/unpaid rent/cleaning fees/etc. at move-out.

Roof was replaced 5 years ago and looks nice. 3 of the 4 water heaters are under 2 years old.

When it comes to reserves, I dont use percentages for capex, I use real dollars, based on the age and life expectancy of large items (roof, hvac, water heater, and a buffer for other items).

He was used to a 1 1/2 page contract that covered "everything" (but really didn't).

We're talking new roofs, new interior layouts, bathrooms, kitchens, everything. 

The original plan was for the tenant's side to pay 100% of the mortgage / taxes / insurance / PMI, while I cover trash and water for both sides. 

You'd certainly want to have an umbrella policy in place, in case your business insurance policy doesn't cover everything.- You mentioned mobile bathrooms (hopefully not port-a-johns). 

Rent covers a lot of different expenses that new LL's don't see going in, then try to recoup from tenants.