And I’ve actually considered upgrading to an M2 Max as I kind of regret only getting 32 GB of RAM in the M1 Pro. However, the trade-in price from Apple is too low.

Apple trade in values are always low. Look around for other options or consider selling directly to someone.

Yeah, if I had an older machine I would. The advantage of a direct trade is no downtime. Apple trades have worked well enough for me in the past, but I wouldn’t benefit from the new machine enough to take the lower price.

> because the Intel/T2 TouchBar machine was so crash prone, glitchy, and hot. The i9 was the worst Mac I’ve ever had.

I'm running the same machine, but for me it's the best Mac I ever had. Decent keyboard very similar to my prior 2015 MBP, larger screen while at the same time keeping the exterior footprint of the 2015, it can run virtually everything you throw at it (sans 32-bit legacy games, but not because of the hardware), and if you remember to restart MS Teams after a videocall (because Teams "hogs" the external GPU and doesn't release it after a video/screenshare call ends) the battery lasts hours, even after three years of extremely intensive abuse.

The only (but massive) issue I have with all post-2013 MacBooks is that their storage cannot be easily recovered in another machine in a disaster event, and with the 2019ff it is completely impossible "thanks" to Apple soldering the flash chips and locking the encryption keys in the T2 processor - without TimeMachine and an expensive NAS you're completely and utterly fucked.

Switching to an M-series Mac would provide me with even longer battery life and probably a notch better performance with IntelliJ, but that's it - I'd have to give up on running x86 Docker images which is a real problem as a lot of third party images don't provide ARM images.

AMD64 Docker images generally work fine, and have recently improved with the integration of Rosetta 2 with Virtualization Framework. It seems to just work, and the performance is much better than when Docker was emulating things through QEMU.

Same for me. My 2018 15" MacBook Pro has been great. I use it every day and have had almost zero issues with it. It has the "bad" keyboard and it is only now starting to act up. I still have AppleCare on it and plan to bring it in and have the keyboard replaced. Hopefully it will last another 5 years after that. I do suspect it will only get one more MacOs update though. But, I have some older machines that still run just fine on Catalina.