Without an actual price quote, this is about where I am; same reasoning. The digging up of asphault and pavers makes it more complex, but this is even for basic service. We only have to pull one wire and put in a subpanel, I think... but IANAE.
So...would you pay the extra for the twin chargers when buying the car??
If you are having to do excavation, that can be a major part of the expense. I plan for the future, and it's usually a good investment. Plastic conduit is pretty cheap these days, so I would put your wires in conduit (a little more vermin protection), and then put in a spare, empty conduit. Specify minimum 2' radius sweeps; most contractors know to do this, but I assumed that once and got 90˚ elbows... For service, price 100A, 150A, and 200A choices with a sub-panel in your garage. More EV's are probably in your future. On top of that, is there a chance that you would put solar on that detached garage? The sum of the feed into the panel and the Solar PV inverter feed must be less than 110% of the panel bus bar rating; you may want the panel to be a size larger than your feed.
It's a bit of a luxury, but an HPWC is a cleaner, more convenient, and perhaps safer, charging setup than a 14-50 and a UMC. I lived for a year with a UMC, then got a deal on an HPWC that someone was selling. I had capacity in the garage sub-panel (pre-planning), and put in the HPWC. It was a wonderful upgrade; I should have started that way! In fact, it was so great, I ordered another HPWC and put it in my second home!
As for dual chargers, High Amp J1772's (HAJ's) and HPWC's are the minority in the wild, but when you get to one, it is VERY nice to charge at twice the rate. Examples of HAJ's are the Sun Country Highway across Canada and Washington State, I have helped get two JAJ's in Pagosa Springs, CO and Salida, CO, and there are others out there. For HPWC's, Tesla is discounting or comping HPWC's for
Destination Charging, and most Tesla Service Centers and Show Rooms have at least a couple of HPWC's.
You may not use them often, but it only takes a few charges in the wild, done at half the time, to appreciate your investment in Dual Chargers.
Good Luck with your new S!