Periodic reboot/recycle of any server type device (once A week or so) is almost always a good idea.
My Linux (Fedora Core 12) music server has been up for 235 days straight. The last reboot was when I cleaned the dust out of the box. Didn't even reboot when I upgraded to LMS 7.7.1.
The Touch and SB3 have been on the entire time, too, without a reset. My SB Radio and the SB Controller are the only ones that periodically need a power reset - perhaps every other month or so.
I find the Squeezebox system, including the server software, remarkably stable. A lot of people use their music server PC for other tasks. That can complicate issues through no fault of the SB software.