I don't think that should necessarily be the case. By persisting resources in the cache after they are changed on the server there is an implicit promise of broken user experiences, since there is no control over which files are loaded from cache and which ones are not (so even for "harmless" images users will see mismatched artwork in the real world). Whatever caching strategy is used for production servers, it should involve a way to make sure users are fetching the latest version of a resource. The dev server can be configured identically and it will still do the right thing. Admittedly when you throw CDN's and other intermediates into the mix it becomes harder to have matching environments, but differences should be minimized as much as possible as a matter of development policy.

My dev server is set up identically to a production server, except that no concatenation or minification is done. I'm not happy with that last compromise, so fingers crossed that HTTP/2 gets here soon and we can stop concatenating, minifying and otherwise perverting our code and resources.