So, I took a look at the site this weekend to see what kind of shape 
things are in.  Bullet points:

   1. Clicking on a feature doesn't work (ie, no popup).
   2. Browser-side caching doesn't seem to be happening.
   3. The folks from the Obama campaign have yet to get back to us with
      the data their interns have presumably struggled so long to obtain.
   4. We don't know what the story is on how frequently they want to
      update the site, or how the workflow on that is going to be.
   5. I improved the 'update the website' process a bit. Details further
      down.

Now, to go into a bit more detail:
1. This looks to be a two-fold problem; OpenLayers is not properly 
encoding the request (it looks like an <ogc:Literal> is required around 
the geometry in the filter), but GeoServer is usually pretty lax about 
that.  GeoServer, however, won't reproject an entity in the filter 
that's not a full-fledged Geometry, and apparently that excludes those 
lame <gml:Box> things.  I can hack up a custom geoserver build that 
fixes this, but don't expect the patch to be in svn anytime soon. 
@sbenthall: How hard is it to get OpenLayers to use a <gml:Polygon> for 
clicks instead?

2.  I seem to remember Arne explaining his triumphant addition of eTags 
on the tiles returned by our instance of tilecache, so this should be 
fixed.  I'll look into it a bit more this weekend.

3. ...

4. I am currently thinking that we need to automate this.  If they're 
going to be updating multiple times over the next few weeks, then the 
couple of days response time that we've been providing will eat up a 
pretty large chunk of the time that each update is relevant.  Probably 
we can ask for them to provide their data in .csv format or as a 
shapefile and hook up a small shellscript that pulls the data into 
GeoServer.  Validation seems like a hassle; but we have port 25 open on 
obama.kepp.net so we can just have whatever we setup explode noisily on 
the slightest strangeness in the input and send an email to Craig with 
the dev list cc'ed.

5. I set up an hg 'changegroup' hook on obama.kepp.net.  When you push a 
changeset, the server now finds the tag prefixed with 'live' that sorts 
last and makes a copy of that the live site.  The idea is that when you 
get your local checkout working like you want, you commit that locally, 
and then do: 'hg tag live-`date --iso-8601`'
and push your changeset.  (All the tags so far have been named that 
way.)  Feel free to try it out and let me know if anything goes wrong, 
would be good to work the kinks out asap.

-david