You need MSIs and PSExec. It's the best deployment system I've used. The MSI configures your server, alerts you to missing dependencies, ngen's your DLLs and loads them into the GAC. If you tag your MSIs with the build number you've also got easy rollback.
There are a couple gotchas that generally require writing an MSI helper DLL but it's no biggie. The only PITA is that if you precompile during the build stage you have to know the path of the application in advance.
Then you just use a little VBScript to let PSExec work it's magic. Maybe I should put together an MSI that installs all the stuff you need to make it work.
Email me if you want some help setting up an MSI / PSExec based deploy system.
No offense intended, but that sounds like an absolutely terrifying solution for deploying a website.
Edit: to expand on my sentiment, this doesn't really seem like the sort of thing that an msi was designed for; and, having to potentially crank out some one-off vbscript seems scary at best.
It's pretty easy, most commercial DLLs are signed, and most open source projects that aren't simply get compiled from source. MSI makes it super simple to add as DLL to the GAC. You do need versioning support in your DLLs but once you have the infrastructure in place it's not a big deal.
There are a couple gotchas that generally require writing an MSI helper DLL but it's no biggie. The only PITA is that if you precompile during the build stage you have to know the path of the application in advance.
Then you just use a little VBScript to let PSExec work it's magic. Maybe I should put together an MSI that installs all the stuff you need to make it work.
Email me if you want some help setting up an MSI / PSExec based deploy system.