Windows is free to download and try. You don't have to enter a product key - just hit next and add it if you decide to buy it. You get it for 30 days. Here is the URL if you want to try it (windows 7 x64 professional):
http://msft.digitalrivercontent.net/win/X17-59186.iso
There is a live CD but it's only used for recovery. There isn't much of a market for trying Windows.
Drivers. Windows update always handles these for me at least. I haven't had to bother with driver fiddling for years. Not only that, 99% of hardware I've worked with recently just works out of the box anyway.
Package manager. Yes there is - there is just no pick and place repository like Debian. You can get packages from Windows Update though. The package manager is called Windows Installer and the packages are MSI packages.
Everyone installs K Lite Codec Pack and media player classic these days (or VLC) almost as a first item to install. Same as you install win32-codecs on Linux.
Maildir import. You stick an IMAP server on your Linux box and copy all the shit to your PST.