When developing an app, you need to create what are called "ad hoc distributions" - builds that are not loaded from the App Store and people just just drop them on iTunes and then magically appear on their iPhone or iPod Touch. There are two things required to make this happen. One is a provisioning file that tells iTunes that your device is allowed to load this program and the other is the program itself (which is a directory containing all of your files). It's a simplistic but effective way of distributing applications.
There are two quirks to this process. The first that I ran across was something I had known but forgotten - Mac ZIP files are different from Windows ZIP files. They have extra files that make uncompressing them normally impossible. You have to actually uncompress them by hand (the curtain begins to reveal the real Wizard of Oz). But that's no big deal - I'll just have to repackage them for Windows distributions. The second is that the provisioning files can't just be "dropped onto iTunes" on Windows. Drag and drop on Windows is a relatively hand-crafted experience and files ending in ".mobileprovisioning" don't make the cut for "drop targets". :) What this means is that you can't drop the provisioning files onto iTunes, you need to add them to the Library manually. (Perhaps you can drop them onto the Library itself, but File | Add to Library worked better for me). And now we can see the short man behind the curtain.
So while I was spooked that Windows and iTunes 8 weren't going to work, they do. Because I'm an idiot sometimes who doesn't try more than a few paths to get something working. Because I've become dependent upon the magic working. And I've become more than a little Pakled sometimes.
Regardless of all of that, I do now have things working from Windows and I can stop messing around with iTunes on my Mac (which was taking for-freaking-ever to add songs to the library). And with alpha only 4 days away, I have LOTS to do - especially since I'm taking the 4th off to go to Elitch's with the family and fireworks with my parents. Cogito ergo sum. And I'm a little scared by that. :)