The asp.net 4.5 bundling feature looks interesting. I wonder how that would play with the way Orchard uses dependencies to determine script ordering?
Combinator is solves some of these problems. I believe it changes the name if you change the timestamp of the file, it doesn't check to see if the contents actually changed. Usually that means the same thing, so mostly a moot point.
If one wanted to get fancy you could use a CacheDependency to watch the static resources and recache them when the contents changed. You could then get away with using the hash of the contents in the bundled/minified file name. Potential gotcha: I'm not
sure if CacheDependency would work with the file system of cloud hosts like Azure or Amazon.
There's another project out there, I think it's called SquishIt that does something similar. Might be worth looking to see how they do it. Cassette requires some xml style comments in the files in order for it to detect dependencies and include them in the
Another problem I had recently was that Combinator isn't used in the admin theme. I made changes to the TinyMce config and deployed them to my staging area. My content editors had some old .js/.css cached and couldn't see any buttons on the TinyMce toolbars.
I had to look into it, they reported it as an IE bug at first but finally figured out that they could fix it by clearing their browser cache. Not sure how we should handle that, but Combinator doesn't help in the Dashboard.