Due to the recent debacle with Hotmail (as well as Gmail, Yahoo and AOL) account credentials being leaked, using a password manager now is more important than ever. I recommend using KeePass Password Safe. One feature in this software is the ability to use password generator profiles. This makes for password changing easy and quick when you need to do it.

For example, Hotmail and AIM/AOL Mail only allow for 16-character passwords. If you set a password generator profile to only generate passwords of that size, any new password you create will always work.

See video below for details. Creating passwords in this fashion makes them a whole lot easier to manage.