As you've said it can be an MSI, I'd suggest going down that route.
You could play around with installer projects in Visual Studio (if you have it; I'm not sure if the Express editions support making installers), as they'll quite happily produce an MSI that will do what you're asking. It's worth noting they'll produce an EXE and an MSI, you only need to distribute the MSI though.
Failing that, take a look at Windows Installer XML (WiX) as that will let you hand sculpt an MSI that does exactly what you want it to do and will cater for all five of your points above.
Note: Using an MSI will mean that you'll need to have Windows Installer on the machine you're installing to - It's in-box from Windows 2000/ME upwards.
