Some updates.
In the forum, I found some items about sync'ing to an iPhone or Touch using something called playlist sync to iTunes in the forum, but labeled "Export to iTunes and iPhone" in MC.
Here's what I did to make it work.
1) I moved my iTunes library files to a backup location. The reason I quit iTunes was that the library was so large that the software became painfully slow (90 seconds of latency any time I changed something on a 4.2GHz machine running off SDDs). So the only way I was going to use that lousy software again was on an empty library.
2) I opened iTunes. I tried with iTunes not running because of the latency problem - loading the software took about 5 min before I cleared the database. When I tried this with iTunes not running, I got an error message that said the iTunes SDK couldn't be loaded and the software wouldn't work without iTunes installed. You may want to change that error message: iTunes is installed, the software won't work unless iTunes is running. At least, not on my machine - Win10, MC27, iTunes 12.10)
3) I opened MC27
4) I attached the iPod Nano 5thG I had previously gotten MC27 to recognize the iPod and pretend to update it. MC27 pretended to update it again.
5) I highlighted the playlist I wanted to transfer.
6) I selected File>Export to iTunes and iPhone
7) In the window that popped up, I selected the iTunes Library. The window also shows the iPod and I tried selecting the iPod only, but got this error message: "Please select one or more destinations" - you may want to update this error message to read "Please select the iTunes destination, because even though we are showing the iPod as a destination, we don't accept it as a destination." I can't figure out how to insert an image, or I would show you the error message on top of the checked destination.
8) The playlist and file locations were imported into iTunes.
9) I used iTunes to update the iPod.
That's a fairly painful process, although with an empty iTunes database, and an 8Gb iPod, I can live with it. I'm dreading the next step of trying to do the same thing with my 128Mb iPod Classic. I'm hoping that only the first time will be really painful. For podcasts, I don't care - listen and dispose - but for the music, I'm trying to manage play counts and ratings. I'm assuming, since those are tags in the MP3 files, that when I sync the iPod to iTunes, iTunes will update the files and MC27 will see that. Can anyone confirm?
*** Further updates ***
The sync process does not work correctly. Playcounts and ratings are not being updated at all in iTunes from the iPod, and they are being updated incorrectly in MC (attached to the wrong files). I have a separate thread with the details.
--------------
I tried updating an iPod Classic, 5thG.
It loaded files up to the iPod (it did not remove files from the iPod) and it correctly adjusted the playcount and the ratings when I sync'd again - both tracks that I uploaded and tracks that were already on the device. (Thanks RoderickGI)
********************
I hope that this is helpful for anyone else new to MC and struggling with the same things. Please feel free to tell me what I'm doing wrong or make suggestions and I'll update my workflow in this message.
Thanks
-T