Hey, the squid server is crashing when i start it.
I used to have the exact same problem! I REALLY need to write a guide on how to install videocache on pfsense. I spent a couple weeks trying to get a working setup. And now, its finally working.
What you need to do is you need to be sure that /usr/local/www/videocache is linked to your videocache directory (/cache/videocache in my case). Then, run ls -l on your videocache directory, /usr/local/www/videocache, and /var/log/videocache.
They all should be owned by proxy:proxy and they all should have read/write privileges.
What I noticed on my setup was that /usr/local/www/videocache was owned by root:wheel even though I did chown -R proxy:proxy on it. The -R command was not working and I needed to force it. So, I did chown -fhv proxy:proxy /usr/local/www/videocache.
My thinking is that since /usr/local/www/videocache is a symbolic link, the -R option is not enough to do it.
I've had a working setup for a while now... on pfsense 1.2.3.