Taxee,
If you reinitialize your iPod, you will lose all the files on it. If you want MC to recognize your iPod without warning you about the reinitialize, create a file called iTunesBackup and copy it to your iPod_Control\iTunes folder on your iPod. After you do this, you will be able to download tunes from iPod to your PC. However, the ratings will not be present after you import them into MC because iTunes does not write that information to the file tag.
If you want to get the iTunes ratings into MC you will need to get the files on the PC and imported into MC. Then if you access the iPod from MC and use the synchronization feature (right click on the iPod drive letter) with the option to 'Sync Data to MC' selected ratings from iPod will enter MC if the rating for the file in MC is not set.
2. Should I convert to MC first on the system on which I have iTunes installed and then download the files to my second computer? How do I do this safely?
It depends on what you are trying to do. If you are trying to use iPod as the way to get files to PC 2, you do not gain anything by converting to MC first.
3. Can I synch with iTunes on one computer and MC on another? or will re-initializing with MC mean I can't use iTunes? (this may not be the end of the world as long as I can get my ratings info to MC)
You can, but we do not recommend going back and forth between iTunes and MC it can be problematic.
Here is the deal.... I think you are trying to get files from iPod to your PC and get MC running on that PC without losing your iPod ratings. Here is what I would do....
1) Copy the contents of the iPod_Control\Music directory from my iPod to the new PC.
2) Install MC and import the contents of that folder into MC.
3) Synchronize all files with 'Sync data to MC' checked.
This should work, but has not been tested extensively. We generally recommend switching to MC and minimizing contact with iTunes and a reinitialize the first time through. Give it a whirl but be sure to back up all your data in case this process fails.
Steve