I usually ignore my server, and just use it, it's only when I log into via ssh that I see a new kernel has been installed. I also only reboot, when I think about it. There is no access to this server from the outside world, so there's no problem with only rebooting occasionally. As you can see from the uprecords output, I've had several kernals installed:
Code:
uprecords
# Uptime | System Boot up
----------------------------+---------------------------------------------------
1 98 days, 19:58:28 | Linux 3.2.0-53-generic Wed Sep 11 20:20:19 2013
2 54 days, 07:33:04 | Linux 3.2.0-39-generic Thu Mar 28 14:00:52 2013
3 48 days, 00:51:53 | Linux 3.2.0-57-generic Thu Dec 19 15:19:27 2013
4 43 days, 11:40:26 | Linux 3.2.0-34-generic Fri Dec 7 11:24:15 2012
5 32 days, 01:57:36 | Linux 3.2.0-39-generic Sat Aug 10 18:22:56 2013
6 25 days, 21:37:33 | Linux 3.2.0-36-generic Sun Jan 20 15:05:28 2013
7 21 days, 03:24:31 | Linux 3.2.0-39-generic Thu Jul 11 17:41:29 2013
8 12 days, 22:32:40 | Linux 3.2.0-37-generic Fri Feb 15 12:42:21 2013
9 12 days, 17:49:17 | Linux 3.2.0-38-generic Sat Mar 2 16:05:51 2013
10 11 days, 19:51:40 | Linux 3.2.0-39-generic Sun Jun 2 19:38:53 2013
----------------------------+---------------------------------------------------
-> 16 4 days, 02:47:31 | Linux 3.2.0-58-generic Wed Feb 5 16:09:46 2014
----------------------------+---------------------------------------------------
1up in 0 days, 16:34:33 | at Mon Feb 10 11:31:49 2014
t10 in 7 days, 17:04:10 | at Mon Feb 17 12:01:26 2014
no1 in 94 days, 17:10:58 | at Thu May 15 13:08:14 2014
up 424 days, 12:05:30 | since Fri Dec 7 11:24:15 2012
down 4 days, 19:27:32 | since Fri Dec 7 11:24:15 2012
%up 98.879 | since Fri Dec 7 11:24:15 2012
The last time I cleaned out old kernels, there were three to be removed after I determined that it booted into the latest one successfully.