When we switched over to auto-set back, limiting thermostats I had a tenant call me and ask why he couldn't get the thermostat up to 80 degrees (max 71).

Ive sealed 1 garage bay as AC'd workspace for mechanic/painter/gym space.

I took out a 1 million dollar umbrella policy which costs about $150/yr and probably nets out to around $100 or less when considering the small savings on my auto insurance plan that goes with it.If you're deadset on the LLC/commercial route, I've heard good things about Bridgewater Bank and Community Resource Bank - have yet to work with either of them though.

The only difference I could see is that the home is more renovated, but all 3 of our bathrooms have been fully renovated with similar finishes in last 2 years, our kitchen was renovated with very similar quality, mechanical ages all very similar. 

If I were in your situation, I'd do either auto withdrawal from their account or online payment. 

The taxes are low because it's in a rougher part of town and Romley St. backs up to a salvage auto yard.But as you have stated, there are still some deals that pop up here-and-there on the MLS, but a lot of them are artificially priced low in order to drive up interest and create a bidding war.

There are some products out there with auto renew options at a fixed spread but haven’t looked too closely at those.

I'm likely going to want to upgrade some of the mechanicals, including the electric panel (it's fuses) and furnace, possibly the HW heater as well.My question is, what would you do in terms of remodeling the space?

Once that starts you will need to get the normal electrical, plumbing, and mechanical permits. 

I have a full time corporate job with a Tech/Auto company of my dreams!