Here are some things you can do to minimize freeze prevention effort.
1. Use a submersible pump so you don't have to worry about draining a jet pump.
2. Put the line from well to tank below the frost line.
3. Put a tee where the well-pipe turns to the pitless adapter, and put a drain valve on that tee that can be operated from above ground. You can probably put a boiler drain in the up-pointing run of the tee and operate it with a shaft that goes through the well cap.
4. Use a bladder tank, which is easy to drain.
5. Pipe the water supply, both hot and cold water, so all pipes can be drained easily. Include a valve at the highest spot to admit air when the pipes are drained.
I suggest using 1/2" copper for water supply pipes in the house because it will be a lot easier to avoid low spots in the pipes.
When you shut down the system:
1. Turn off power to the pump.
2. Open all valves and faucets, including all shower control valves.
3. Open the drain valve in the well
4. Open all drain valves in the water supply lines.
5. Make sure the water heater is drained. The water heater should have a vacuum breaker to avoid risk of collapsing it if you drain it without opening a hot water faucet.