Any other advice or suggestions I haven't considered above?
You will have a few months from when production starts until your car is delivered (maybe only a month or two) but plenty of time to have an electrician come and install what you'd need. I'd definitely consider getting a separate 240V 50A circuit installed for your Model S and as you said you may get a second EV some day, go ahead and have them install a second plug too since labor costs much more than the parts. That's what I did in my garage (2 separate 50A NEMA 14-50 outlets).