Well, I haven't made it terribly far on this project. More testing and reading than anything else. However, I could very well have a decent and inexpensive solution to this problem.

I've been going through trying to determine exactly which apps need to be managed and on how many workstations. Most of the apps thus far are third party apps that are not public.

As it turns out, most of the public apps that we do use have MSI files out there. So, I've been testing deployment of software via Group Policy. So far, everything has been going great. In the past, this was impossible due to the horrible WAN links I had. However, that is no longer a problem and I have a very decent distributed file system up and running for software deployment.

I've been playing around with http://www.advancedinstaller.com/ to repackage the third party apps that won't provide us the packages as MSI. It's quite a pain to go through and determine every file and registry key that is installed with the free version, so I may end up purchasing the enterprise version. It's only $500 and so far it's repackaged the dozen or so apps that I've tested without a problem.

Some of the third party apps that I've looked into cost about $6000 just in licensing just to manage ~200 workstations. That's not including parent and child servers... So, I think that approach may be a waste.