Thank you Gabe, you have saved me an immeasurable amount of head scratching
and difficult decisions. Your link above seems to work perfectly and I now
have roller running at localhost/mywebapp/roller. As a quick summary in case
it is of use to someone:

In $TOMCAT_HOME/conf/Catalina/localhost you need the primary context of
'mywebapp' which is just a standard context fragment named 'mywebapp.xml'.
For the secondary context, put a file in the same location called
'mywebapp#roller.xml'. This again is a standard context fragment but it is
important that the docbase of the secondary context is outside of the
webapps as the '#' syntax is not designed to work  inside of the webapps
folder. I am not sure if it is necessary to have both contexts outside of
the webapps folder for this to work but in my case, I did. I found if the
secondary webapp was inside of the webapps folder the server would throw an
error on start. My first context fragment was:

<Context
docBase="/mnt/storage/gavin/work/svn/tootired.net/trunk/web/build/web"
path="/tootired.net"/>

and the second one for roller was:

<Context docBase="/home/gavin/Desktop/roller" path="/tootired.net/roller/"
/>


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