If you are outsourcing your IT, and you have servers set up with softlayer or server beach or other place, how do you recommend handling updates to Windows as well as software running on those machines?
Do you ask them to automate it and apply all the updates? Do you ask for a manual update where they assess the impact of the updates on your running software and applications (say your .Net based site, or SQL Server)? Most importantly, do you ask them to immediately apply the updates as soon as they are available, so that you're more secure, or do you wait to see if the update caused problems with other servers first? Assume that we don't have any test servers - just a bunch of production servers.
We're having some trouble deciding on a good approach, and can't have a dedicated IT department or even person.