I found an app in the marketplace called "TuneSync" that actually integrates with iTunes and allows you to select playlists from your iTunes library to sync with your phone, and it does it using your wifi so no need to even mess with plugging the phone in. There is a "lite" version but it only lets you do 20 songs at a time and the paid version is only $4. I have to say, this thing does everything I want and does it painlessly. Now all of my **bleep** devices can just play nice and I don't have to deal with 35 programs to make each one do what I want it to do.
As a side note, my phone has started replacing things around here. There may soon be a few Apple devices that are either sold or relegated to my "Gadget Graveyard", which is actually just a drawer under my desk where things that I used to think were cool go to die. The iPad already found its way into someone else's hands due to the fact that it wasn't as cool as I thought it would be and now a couple iPod Touches may end up in the drawer since my phone is more than capable of bringing my music along with me. Sad days for them.
I found one that I like a lot as well....it is call Doubletwist....it integrates both WMP AND iTunes and syncs to an Android phone as well and other devices too such as PSP and others... http://www.doubletwist.com for more info