This was one of the major blockers that iirc Mozilla threw in the way of zstd compression support: they said zstd with a standardly accepted dictionary would be too particular & wanted more. With this spec maybe Moz will accept zstd as a web compression standard.
We see similar fixedness in the field all over the place: people freaking love small Docker image sizes & will spend forever making it smaller. But my gosh the number of engineers I've seen fixate on total download size for an image, & ignore everything else, is vast. Same story, but server side: my interest is in the download size for what v1.0.1 of the Docker container looks like once we already have v1.0.0 already shipped. Once we start to consider what the ongoing experience is, rather than just the first time easy-to-judge metric, the pictures all look very different.
Then there's the other thing. The performance reasons for bundling are being eaten away. Preload & Early Hints are both here today & both offer really good tools to greatly streamline asset loading & claw back a lot of turf, and work hand-in-glove with import-maps. The remaining thing everyone points out is that a large bundle compresses better (but again at the cost of making incremental updates bad). The spec is in progress, but compression-dictionary-transport could potentially obliterate that advantage, either make it a non-factor, or perhaps even a disadvantage for large bundles (as one could use a set of dictionaries & go discover which of your handful of dictionaries best compress any given piece of code). These dictionaries would again be a first-load hit not different from a bundle's hit, but could then be used again and again by users, to great effect again for incremental changes. https://github.com/WICG/compression-dictionary-transport
Bundles are such an ugly stain on the web, such an awful hack that betrays the web's better resourceful nature. Thankfully we're finally making real strides against this opaque awful blob we've foisted upon this world, our users, and ourselves. And we can start to undo not just the ugliness, but the terrible performance pains we've created by bundling so much togther.
People harp on and on about the benefits of bundles for compression, but man, it's so shortsighted & stupid. It favors only the first-load situation. If your user actually comes back to your app, these advantages all go away, disappear. Personally I'd rather help people that use my app regularly.
Second, the days of bundles being better at compression are numbered. Work has been ongoing to figure out how to send compression dictionaries separately. With this, 98% of the compression advantage disappears out the window. https://github.com/WICG/compression-dictionary-transport
Neither of your approaches sounds like what I'd do. Personally I would build an http server that takes raw uncompressed source. When asked for a file the first time, it compresses & builds the dependency maps in parallel, & saves both of these out, maybe a .gz with some xattr on it. Or store that data in memory, whatever. The first user gets a couple extra ms hit, but the server transparently still does the thing. Developer mode is just a tool to watch the file system & clear those caches, nothing more, & can potentially be completely separate.
Bundles are just so awful. They complicate what used to be an elegant understandable clear world of computing. We can & should try to get back to resources, if it makes sense. And the cards are lining up to make this horrible un-web un-resourceful kludge potentially obsolete. I'm excited we might make the web make sense again for end-users. They deserve to be out of the bad times.