Thanks for the quick answers Michael, I'm afraid they've thrown up what
looks like a bug to me.  It's similar to this bug but I'm happy to open
a new one if that's more appropriate.

Following your answers I set the following in rsyslog.conf (plus all the other 
parts obviously):
$FileOwner syslog
$FileGroup adm
$FileCreateMode 0640
$DirOwner syslog
$DirGroup adm
$DirCreateMode 0755
$Umask 0022
$PrivDropToUser syslog
$PrivDropToGroup syslog

I want dynamic files based on severity (among other things but this is what I 
tested) using the following template:
$template tLevel, "/var/log/%$MONTH%/%$DAY%/%HOSTNAME%.%SYSLOGSEVERITY-TEXT%"

I sent a log entry with:
logger -p local0.debug 'debug test'

and this resulted in the following syslog entry:
Nov 16 15:37:27 robbie rsyslogd: Could not open dynamic file 
'/var/log/11/16/robbie.debug' - discarding message

although ls -l /var/log/11/16 showed:
-rw-r----- 1 syslog syslog      0 2009-11-16 15:37 robbie.debug
-rw-r----- 1 syslog adm    156681 2009-11-16 15:35 robbie.info
-rw-r----- 1 syslog adm       622 2009-11-16 15:37 robbie.syslog

Yesterday when the only difference was:
$FileGroup syslog
$DirGroup syslog

robbie.debug was created and written to as I expected.  Just in case it's 
relevant I restarted rsyslog after editing the config with:
service rsyslog restart

robbie.info and robbie.syslog were created overnight owned by
syslog:syslog but I did a chown before the test I've described here.

The 2 things that look like bugs to me are:
- creating robbie.debug with the wrong group
- rsyslog being unable to write to it even with the wrong group.

-- 
[karmic] Messages not being sent to system logs
https://bugs.launchpad.net/bugs/407862
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