This sounds like a terrible situation, but I wonder if a weekend of Claude iterating could improve on any of these problems. They seem to have been pretty successful on the Mac M series.
It probably will help you maintain a better local fork, but getting all things upstreamed is the bottleneck and won't help too much here.
I'm sure Claude would be capable to solve many of these. But the next machine probably requires the whole dance all over again, and it just doesn't scale very well, I feel.