Starting with 0.4.0, the bitcoin releases on Win32 will be generated deterministically (assuming me/devrandom have enough time to code the specifics) and signed by all the Bitcoin developers who have the ability to do so. The "installer" will then install a minimal script and the relevant dependencies to the Bitcoin folder and then run that script. That script then downloads the latest version of Bitcoin and checks that enough signatures are on it for it to be considered trusted and install that version. The script will (hopefully) also be used to update bitcoin when new versions come out.
On code signing:
This one is a bit more difficult. Because Bitcoin will be built deterministically, we have two options. A. send the code signing private key around to all the devs for that to be a part of the building process (this is even harder as the building happens on Linux via the MinGW cross compiler) or B. find a way to strip out the code signing certificate in the download script and then check the stripped version instead of the signed version. I googled this pretty quick and saw no simple CLI program which will do this, but I might have missed something as I didnt spend too much time on it. If anyone finds something, please tell me.