http://installpad.com/
This program is amazing.
I will admit though, there is a little setting up but once it has been setup (and you just keep a copy of your config backed up somewhere), this program is a fuckin gem and if you have say, 5-10 applications that regularly gets updates, this will certainly make it a lot simplier.

Imagine this: Creating an XP image or Windows 7 or whatever the hell the kids are into these days and having the install set up so you can have it not only unattended (meaning it is pre-configured so you do not have to enter in time zone and the Windows key, etc) but after the install just have a bunch of tick boxes with the option to install most commonly used applications and then having this progam on top to download the latest version for you. Hypothetically speaking, if the image had MSN Version 7, InstallPad would jump in and update that to the nasty MSN version live or 9 or whatever MSN uses these days.

It would take a lot of effort but man, that would be sexy. It would be worth it on a new OS which you know will be around for years to come.

There is such a thing. It is called Windows XP Black Edition but it is mising InstallPad - a cruicial component missing.