I'm moving from SQL Server 2005 RTM to SQL Server 2008 R2 and 2012 in the near future.

The server has about 25 Databases on it and they are all on the new Server..

I really don't want to perform any upgrades for I do not want anything to go wrong. I know the risk is low but I do not know what has been to that Server. Reboot and it does not come up I loose a customer.

A bunch of stuff does not work. e.g. I can run a job based on a maintenance plan which is a pain.