Installation and Value
Plugging in
The installation of the Freestyle was effortless. I downloaded the latest drivers for it from the Microsoft site, and ran those after plugging in the Freestyle into the game port of my sound card. The pad was detected and worked immediately. The Wingman installation was a bit hairier. Since our pad came with a gameport to USB adapter, we tried plugging it in a USB port rather than the gameport. Windows detected a new device but when we tried to point them to the drivers on disk, it wouldn't take. No problem - we canceled that and ran the install program off the CD. Mostly it worked well but when Windows recognized the new device it again tried to install a generic USB device. We canceled that and were bothered no more.
Installation: Advantage Freestyle
While the Wingman's installation was pretty easy, it did get a bit confusing with Windows trying to install a random USB device while the real installation was going on. Perhaps this may not have happened if we plugged it into the gameport, but MS's installation process was just a bit easier.
Is it worth the dough?
MS sells their Freestyle Pro game pad for a whopping $75 US on their website. Yes, the street price is closer to $60 US, and the game is bundled with the full version of Motocross Madness, but $60 is a lot to muster up for a gamepad, even one with motion sensing technology. Logitech plans on rolling out their Wingman Gamepad Extreme at a much more reasonable MSRP of $40 US, which means that you may see it as low as $25 or $30. It doesn't come bundled with any full games but it will come with a 3 mission OEM version of Star Wars Rogue Squadron.
Value: Overwhelming advantage Wingman
Duh, it doesn't take a mathematician to know that Logitech has beaten the pants off of Microsoft in terms of price. Sure you get Motocross Madness for free with the Freestyle but since it's an old game you can pick that one up out of the bargain bin with the cash you save by buying the Wingman. You'll still have a lot of change leftover too!