That would work with me. And i'd love to have a neighbor with a tractor!
Here's my two cents:
1. Get a bigger house number sign at the end of the driveway.
2. Don't plan on going off grid unless the Quality of Service is so poor. It'll never be cheaper.
3. My last month's home electric usage was 300 kwh, I use Nat Gas for everything. My small vacation cabin which I visit one weekend a month, and keep at 55 deg F, used 1760 kwh for the same month (all electric). Get used to paying for energy. You can investigate LP for your heat, domestic HW, clothes drying and cooking Or consider #2 home heating oil for heating and DHW, but you'll probably need a chimney. Energy is never free.
4. You are not being "double billed" for your electric. About 15 years ago there was a major effort to deregulate the electric utility industry. The Fed Govt felt that with the franchised Utility owning their own power plants, there was no incentive to get the cheapest power for their customers, and forced the utilities to sell off their plants. Customers would then be able to shop for power suppliers they liked (cheaper or greener) and the Utility would just be responsible to deliver it (for a fixed price). That's why there are usually 2 or 3 different parts to the bill. My opinion: Sometimes deregulation works, sometimes it doesn't.
5. The decay at the base of the one pole you photographed does not appear bad. What is a problem is the guy wires appear slack and that needs to be addressed. Also, I noticed the pole has either telephone or cable service attached. This complicates the possibility of using your easterly neighbors pole line in place of your 3 poles.
6. The Power Utility runs distribution lines along the main roads at 4000 to 13000 volts. When it needs to feed a few houses it usually taps that line with a fuse and extends that high voltage line a few pole sections down the road or driveway to a transformer. The transformer brings the voltage down to 120/240 used in your house. In my Utility's parlance for an overhead supply, the wire connection from the transformer to your house (weatherhead) is called the Service Drop, and the weatherhead cable/conduit to your meterbox is called the Service Entrance. The service drop is usually owned by the utility. The service entrance is usually owned by the homeowner. The meterbox is owned by the homeowner and the meter is owned by the Utility. Every utility uses slightly different terms for these parts, but what's very clear to them is "who owns what". My Utility is required by the State Regulators (PSC or PUC) to give a home owner 100' of high voltage line, 100' of service drop, and one pole & transformer if needed (free). Anything extra the home owner needs to pay for.
7. The Utility Planner, who will come out to inspect your situation, has the power of God, and you should be very nice to him. He works for the Utility and has the full and final say in what needs to be done. Did I mention you should be very nice to him. He usually spends most of his time interacting with professional contractors, and probably doesn't enjoy dealing with homeowners cause each one "wants a special deal". Don't be that guy.
8. Relax. You almost made it thru the winter. Maine winters can be brutal. Your power problem doesn't sound like a big problem and the Maine spring and summer are the best. Oh,... except for mud season and the black flies, those aren't the best.
