He has an onsite manager, full time repair person, and a supervisor overlooking all of the properties.

Actually, the contractor part would draw $70G to $90G for a site supervisor (that's what I do) in the mid sized project market i.e. 2-3 story office building, or small school, retail build outs etc.

The loan officer did say she would check on an in-house option with her supervisor tomorrow.

I would bring my main job supervisor through as well

One is owner-builder, second is education+2 years journeyman/higher (in your case, project owner, that makes you supervisor), or 4 years journeyman/higher.

When that failed I asked to speak to her supervisor who wouldn't budge either, so I'm pretty much stuck with having the main in one single location.

I will sometimes call the managing broker (their supervisor) and will get a response. 

The $1,000 electric service upgrade will include a new 125 or 200 amp breaker box (depending on if I decide to go electric or not with the new appliances)and breakers, a new meter box, a new riser pipe and leads and the electrician to pull the permits and do all the work (side job for my workplace's admin's husband).

I'm looking for some second opinions on back of the napkin calculations to compare with my own for two options that I have found for the first new property, located close to my new workplace.

I am a recruiting supervisor for the region and work out of Warwick.