This does not become easier with monkey patching and open classes + lots of meta programming.
I started with Rails during version 1.x and went up to 2.x with it, good fundamentals of Rails have not changed and are the same (inspired others to adopt such as ORM/convention over configuration etc) but lately, I ended up with Go instead for being at least some type system no matter how crude and having a single binary in the end to deploy.
Never have to worry about pip/gem/npm crashing on me. Mostly.
rails new -d postgresql --css tailwindNo pipelines, no minification, no nonsense, just serving js and css directly.
Hey.com works like this, and they reported nothing but improvement.
Bundling is also something that we no longer need to do since the introduction of HTTP2. I would even consider it an anti-pattern these days, since it means you're sending the client much more data than they actually need.
Tree shaking is definitely very important for something like tailwind though.