Do you have first-hand knowledge or experience with these businesses, or are you just looking to stir up trouble? 

If you want to be truly passive while living abroad you could consider a DST transfer or syndication where you transition your properties to professional management and get paid as a limited partner and not have to worry about any sort of property management takes.

I’ve househacked a handful of properties and am currently doing so now.

You have no control over the servicing transfers.

If you have a solid deal in the Finger Lakes (which you have said has high equity growth), keep the bird in the hand. 3.

I was to start assembling a team together and am looking for any recommendations of contractors that will offer a little bit more hand-holding, as I am still fairly new to this process. 

A and B tenants, usually need more hand holding and expect more because they assume that they are entitled to it because they are paying so in rent. 

I don't enjoy being a landlord--I enjoy being an engineer (my day job), so having more than a handful seems crazy.

Germantown has better cash flow potential but may require more hands-on management.

Then make the decision if being a hands on landlord is something you are realistically interested in.