I would rather go all in now.
If a full power HPWC is driving a service upgrade to 400A, I would certainly call that "going all in."
Our home is about 3 years old and has 200A service, though much of that is already used.
When you say "much of that is already used", what do you mean? A full breaker panel, or individual breakers totaling 200A or more, does not require more than 200A service.
200A is a lot, even with car charging. Unless you have serious loads in the house (electric heat, pool/spa pumps, big A/C loads, a large house with lots of lighting, etc), 400A is probably not necessary. I know several people with 400A service, and for most of them, it's not necessary - it's really just "bragging rights" (a lot of my friends are Tim Allen/"Home Improvement" fans)
The required size for a service is based on a load calculation, which is a (potentially confusing) calculation of a home's peak needs. You shouldn't need an upgrade, unless someone has done a load calculation (and shown/explained it to you) that demonstrates your potential demand exceeds 200A.
Are you asking for a HPWC installation, and being told the service upgrade is required? Or are you asking for the install and service upgrade? Two very different situations.
Proposal #2 $7600 is to run the additional 200A about 100 feet to detached garage on a separate panel there then run 90 A off that to HPWC (leaving 110A for future use in garage).
Again, installing a 90A breaker for the HPWC in a new 200A panel doesn't leave 110A left - it doesn't work that way. You could install 10 100A breakers in a 200A panel. As long as the total draw doesn't exceed 200A, you're fine.
I understood the electrician was to use #4 copper for proposal #1 which I previously thought was appropriate, however info in this thread seemed to suggest #2 copper would be recommended. Given that, I have already reached out to the electrician asking about the gauge/rationale, as well as what would be used in proposal #2.
It sounds like your electrician isn't well versed in car charging requirements. #4 is undersized for charging at 72A. If charging at 72A, National Electric Code requires you upsize the circuit by 125%, and install wire/breaker for 90A min (circuits are rated for intermittent loads; the NEC considers car charging a continuous load and requires the 125% safety factor). This would require minimum #3 copper or #1 aluminum. #2 copper is often recommended, since #3 copper isn't often used and is harder to find. Bear in mind this wire is also good for a 100A breaker/80A charging - I would install a 100A breaker and set the HPWC to 80A for future expandability, vs unnecessarily limiting it.
My wife and I expect our MX 90D in a few weeks. Leaning toward #2 as we also have 2 Model 3 reservations.
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How (un)reasonable are the quotes given the necessary service upgrade, distance run, and trenching?
What gauge copper is appropriate in each case?
I can't speak to costs in your area. A 100A circuit is #3 copper/#1 aluminum minimum
Is running the 200A service to a panel in the garage now preferred over only running 90A to HPWC then 18+ months from now possibly pulling another 90A through the existing conduit?
You can't run multiple circuits from the home to a detached outbuilding - NEC requires a single feed with a subpanel in the outbuilding. Even if you could, you'd need to plan ahead an install a larger conduit. Plus, pulling cables through a conduit that isn't empty can be tricky - you would probably want to install a second conduit in the trench for future use.
I separately came across a thread regarding 277V (rather than 240V) being supported with the new HPWC. Given the service upgrade which is being done, is it worth asking for 277V instead?
277V is the nominal line-to-neutral voltage of a 277/480 three phase system. This is heavy-duty commercial/industrial power. It's unlikely that you'd get permits to install this in a residence or that the power company would offer it. You'd probably be looking at 10's of thousands to install, even if you could.
In summary, here's what I would do -
Install a 100A subpanel in the garage, fed with #1 aluminum off a 100A breaker in the main panel. Install a 100A (or 90, but why not 100?) breaker in the subpanel to feed the HPWC. Feed the HPWC with #2 or #3 copper from its subpanel breaker (this is a short run, so cost is less of an issue, and I don't believe the HPWC is rated for Al). When the Model 3's arrive, you can add breakers to the subpanel and add more HPWC's. The newest HPWC can be tied together to share the available charging current.
Only do the service upgrade if a load calculation shows it is needed and the inspector requires it.
Al wire to the subpanel, properly installed and sized, is just as safe as copper, and will save you at least $1000 on a 100 foot run (yes, copper is that expensive).
EDIT: Also, if the load calculations show a service upgrade is needed, consider replacing some heavy electric appliances with gas ones - that will free up some headroom in the calculation, and may be cheaper than a service upgrade.