Ok, never mind, found the relevant information under the Cache Revalidation and Reload Controls section of the HTTP Spec
Basically, you can serve all the different validators you want but you must be aware that in such case proxies may have a set of different validators from their own cache and from various user agents communicating with the proxy. They may choose to send one to you and that might not be the correct or the most optimal one for the end-users. However, a "best approach" has been suggested in the spec.
I suppose this should covers Expires headers as well as ETags, Cache-Control and whatnot.
Here's the relevant excerpt, in case anyone's interested:
When an intermediate cache is forced,
by means of a max-age=0 directive, to
revalidate its own cache entry, and
the client has supplied its own
validator in the request, the supplied
validator might differ from the
validator currently stored with the
cache entry. In this case, the cache
MAY use either validator in making its
own request without affecting semantic
transparency. However, the choice of
validator might affect performance.
The best approach is for the
intermediate cache to use its own
validator when making its request. If
the server replies with 304 (Not
Modified), then the cache can return
its now validated copy to the client
with a 200 (OK) response. If the
server replies with a new entity and
cache validator, however, the
intermediate cache can compare the
returned validator with the one
provided in the client's request,
using the strong comparison function.
If the client's validator is equal to
the origin server's, then the
intermediate cache simply returns 304
(Not Modified). Otherwise, it returns
the new entity with a 200 (OK)
response. If a request includes the
no-cache directive, it SHOULD NOT
include min-fresh, max-stale, or
max-age.