Updating that allows for possible roll-backs

Hi,

I'm sysadmin for a company who's Saas product runs on Ubuntu 10.0.4. I've been getting notifications, recently, that a ton of updates are available for the system: all are listed with urgency=low. Two concerns:

1.) Possibility that one or more updates will break something.
2.) If we wait until a major upgrade is forced by Ubuntu (around 2015, if we want to continue to receive support), that will entail cumulative application of all pending updates. It's much more likely that something will be broken, of course, if a ton of things are changed. So, we want to be as up-to-date as possible, at all times.

I would like to roll out updates slowly over time and have some mechanism for falling back, if a problem arises. Is there anyone on the forum who can point me in the right direction and/or make suggestions?

-Anthony