That's very good to hear that it can be scheduled with the Task Scheduler (and executed by a command line).
2. Yes, you can, via the commandline, start the sync with a parameter where you specifify a playlist or playlistgroup. Only files in this playlist or group will be synced and all files which are removed in MC can be removed in iTunes as well (same for newly imported ones)
Just to be clear, you said "all files which are removed in MC can be removed in iTunes as well". I won't be deleting any files (well, not most files) from my MC library itself, they'll just be removed from the selected set of Playlists.
For example, I have a Smart Playlist that looks like this for my iPhone:
[Media Type]=[Audio] -[File Type]=[cda] [Removable]=0 -[Keywords]=[noipod] -[Rating]=1 [Channels]=<=2 ~mix=1800,6%,{[Genre]=[Alternative]},10%,{[Genre]=[Americana]},6%,{[Genre]=[Classic Rock]},10%,{[Genre]=[Electronic]},3%,{[Genre]=[Folk]},15%,{[Genre]=[Indie]},4%,{[Genre]=[Jazz]},6%,{[Genre]=[Pop]},8%,{[Genre]=[Progressive]},10%,{[Genre]=[Psychedelic Rock]},4%,{[Genre]=[Punk]},6%,{[Genre]=[Reggae]},3%,{[Genre]=[Rock]},3%,{[Genre]=[Trance]},6%,{[Genre]=[Urban]} ~sort=[Artist],[Album],[Disc #],[Track #],[Name]
That's my "main mix" list for my phone. This basically builds a randomly mixed playlist of 1800 tracks using with the Genres distributed using those percentages. So, it looks at the full MC library, and then builds that list, which is what I sync over to iTunes (and then to my phone). I have other lists that are used too, like these:
600 Favorites:
[Rating]=>=4 [Media Type]=[audio] [Channels]=<=2 ~sort=Random ~n=600 ~sort=[Artist],[Album],[Track #],[Name]
200 Recent Imports:
[Media Type]=[Audio] -[Media Sub Type]=[Audiobook] [Channels]=<=2 -[Rating]=1 ~sort=[Date Imported]-d ~n=200 ~sort=[Artist],[Album],[Disc #],[Track #],[Name]
I have five or six of these types of lists. And then I have a "regular" playlist that syncs too (for stuff I want to just "manually add").
So, I need the equivalent of the built-in
Delete from Handheld any files not in the sync list feature. If the file is "in" one of the lists (which will change every time it syncs), I need it to add it to iTunes. If a file is no longer "in" the list (because the randomized lists changed with the next sync, for example, or maybe because I removed the item from the manual list), then I need that track to be removed from iTunes.
Does it do this?
I could work around the inability to convert on the fly by pre-converting and stacking my entire library on a regular basis. But I can't work around this part. I don't want to have to manually delete or add any file to iTunes to get it off of my phone. Like I said, iTunes is a sync engine. I don't even look at the files in it's database except to manually set audiobooks to Media Kind = Audiobook occasionally when I add a new book. I certainly don't want to have to manually remove stuff from iTunes to get it off of my phone (that would be more work than the sync workflow I'm doing now).