DisplayPort Alt Mode via USB-C: finally. This is the biggest missing feature from my Galaxy S9 that I wanted on my Pixel 8.

I'm a diehard headphone jack enthusiast, and yet I still switched to a Pixel 8 (had a Galaxy S9 previously). The unfortunate reality is that just about everything above the "bargain bin phone" price point has given up on the headphone jack (at least in the US market), and the options that do exist (Asus, Sony) have crappy software update policies*. I still hate not having it, but honestly its been a pretty decent phone otherwise. Granted my perception of the price point for it is a little skewed, since I got a 256GB model for $510.

*Plus my carrier sucks and only supports VoLTE on Samsung, Apple, and Pixel...

As someone with minimal skin in the game compared to you fine folks that keep the place running, it seems like option 2 is the most sensible for the time being. If it ends up being a disaster, then going to option 3 makes sense.

I'm seriously considering a 2022 Chevy Bolt in my area (25k miles, $16k after tax credit). I typically buy cheap used cars, but the used market in my area is awful...

This is the one (software) feature I'm still missing from my Galaxy S9; I typically spend a lot of time in places with very poor internet, so the ability to download media and watch it on a TV from my phone is great.