I also agree (generally) about the tax liability and whether the Model S is a good choice. Coming from someone who cancelled my reservation partly due to financial issues even though I could buy several EVs in one year and get the full tax credit.
But - high mileage drivers are the ones that can really make a Model S work. The OP is clearly not a EV zealot, or the extra hours of driving wouldn't be an issue. Or just keeping a third car. Or renting.
One thought, are you sure about Chademo and future plans? We had a few pop up recently near us and I had no idea they were coming.