I'm seeing a similar problem, except that the computer in question has been running continuously the whole time, and it's directly connected to the internet (so no firewalls or NAT-entries that might be timing out).
This is with tor-0.2.8.8-1 (in sid). What I'm noticing is that if the Tor daemon has been running for a while, a basic connection via the SOCKS port never connects. If I bounce the daemon, then a connection works. The daemon is not generally doing anything else: it's pretty idle. I haven't yet characterized how long it must be idle before connections cease to work.. I'll try increasingly long intervals over the next week. The current datapoint is that an uptime of 9.5 days lead to a failure, but a connection that happens one minute after startup works. I *did* see that 'arm' reported 0 circuits open when it was not working, although just a few minutes before my (failed) test, /var/log/tor/log said "Tor has successfully opened a circuit. Looks like client functionality is working.", so it's not entirely idle (but also entirely not working). cheers, -Brian