I was able to solve some of the problems:

I had some old stuff left in an apache config, it was hindering my filter to 
work.

I had to add an  tag in the host config to make it work - I also added a 
context, pointing out the exact WAR in the host config.

I'm still not sure about the last thing - is there another way to do this - it 
seems cumbersome to have the same servlet paths both in Apache's virtual host 
config as well as in web.xml.

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