First up, thanks to Sander for the help on Cherokee. I ended up having to build it myself since I'm using the soft-float ABI, so both sets of instructions were helpful.
Secondly, setting Cherokee to start at boot.
There is a start / stop script in the contrib source directory. (I installed from source, so I had the source directory already. Not sure what happens with Sander's .deb package, but you can always download the source package just to get the script.)
It needs to be copied into the appropriate directory & registered. This should be done with root privileges, so either change to the root user or use sudo before each command:
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cd <whereever you extracted the Cherokee source code>
cp contrib/cherokee /etc/init.d/
chmod 755 /etc/init.d/cherokee
update-rc.d /etc/init.d/cherokee defaults
The last command will give a warning about 'script cherokee missing LSB tags and overrides', which is due to a change in the way Debian handles dependency-based booting. I don't know enough about Debian to suggest how to tweak the script, and it still worked for me, so I would just ignore the warning

When you restart your Pi, you should see a message during the boot sequence about Cherokee starting up, and you'll be able to access your web server immediately!
Finally, here's a link on how to get to the Cherokee admin interface:
http://www.cherokee-project.com/doc/other_bundle_cherokee-admin.htmlI have a mainly headless setup, so I use
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sudo cherokee-admin -b
and then browse to
http://<my PI IP address>:9090 to get to the admin site. This is not the most secure way, but it works for me. See the link for full details. Also note that cherokee-admin must be run as root.
References:
Link to the startup script (scroll down to 'Autostart'):
http://www.cherokee-project.com/doc/basics_installation_unix.htmlLSB:
http://wiki.debian.org/LSBInitScripts/DependencyBasedBoot