Regarding the first question, there is a post in the forums by william_syd suggesting to move 0check4updates out of /etc/cron.daily and into /etc/cron.weekly, but as he says it's not the SME way of doing things.
Regarding the second you can't know until you try it. A safe way would be to not apply the updates immediately, and look around in the forums and bugzilla and see if anybody reports a problem. Also you could setup a test server, and do the updates on it first. However even then it may not restart gracefully, for example I had a server that after restart required me to do a manual file system check to repair problems (that were caused not by the update itself, and were revealed by checks done at restart).
Anyway you won't encounter problems very often, as SME is really a great piece of software, maintained by a dedicated team.