SW Deployment. Surely by now...
..there would be some brilliant, free, solution that just does what you want with a bit of finesse! I haven't needed to pay much attention to this area for a long while, but a lot of you lot must have so where is it then?
SMS's or enterprise products for ££££s with lots of pretty colours and nasty pie-charts appear to be all over the place. Apparent favourites like SpecOps Deploy aren't especially cheap either, it doesn't appear to like 2K8 and the one that allegedly will appears to be a teensy bit delayed. Freebies seem to be limited to MPKG that I like in principle but it's not integrated with AD computer groups, OUs or whatever - you have to keep typing things in XML in files. There are a few fans on Purgos on here, but I can't figure out what may or may not be happening with the v3.0 beta release I can't download and the latest v2.0 won't see the domain to pick any computers (perhaps it's a 2K8 thing).
Then there's good old GPO deployment which pretty much does what you want, especially if you security filter individual packages (rather than entire GPOs) and know how to wrap a *.exe EXCEPT you haven't got a clue whether a package did or didn't install.
So what do you do about package installation status? Throw other inventory tools at the problem? Wait until someone knocks on your door and complains X isn't installed? Ignore it completely? Make custom scripts to talk to WMI or the registry?
Thinking about the latter, very briefly so don't shout too much if it's stupid, it struck me that MsiInstaller does of course write events with timestamps, informative IDs, messages and the all-important GUIDs in the app event log, so you could routinely trawl through the new-since-last-time events at computer startup and throw the fresh MsiInstaller event info wherever you want it. Downside is that event logs can and do die via abrupt shutdowns, but you can detect that and could probably fix it at the same time.. assuming localsystem can clear an event log.
[What's a "holiday"?]