Syncing different libraries and tailoring content for iOS devices.

Hi guys, got a couple of iTunes and iOS Questions.
First a little background info:
I have:
- A 16gb iPhone 4s
- A 32gb iPod Touch (Probably 1st gen. I got it 2nd hand).
I am considering:
- a 16gb or 32gb iPad (Wifi only)
I used to be a PC user, but have recently switched to Mac.
- My PC Library contains all the music and Apps I had up until that change. (This is before I worked out how to use iCloud.)
- My Mac Library contains all the same music, plus everything I’ve acquired since. But NOT the playlists. For some reason when I copied my music to my Mac, those did not transfer.
- My iPhone is now synced to my Mac Library. (Which is the better library, but it lacks the old cool playlists I lovingly made).
- My iPod is synced to my PC library, so it’s missing music, but has those old playlists.
So my questions are:
Is there a way to transfer those old playlists to my new library, and sync them with my iPhone? (Most files should still be present, although the file locations may now vary.)
I want to resync my iPod Touch with my Mac Library, but keep the awesome playlists I have made (Till now, I’ve been reluctant to do this, because my iPod is hooked up to my stereo, and I didn’t want to have to make entire new playlists.)
Is there a way to bring my PC library up to speed and sync it? (It’s actually a different library, with similar files). I’d actually like to (if possible) delete that whole library and start again so it matches my Mac, and keep it all up to date with iCloud. The only thing I want to save are those old playlists. 
My girlfriend has almost the same library as me (The PC Version) on her PC, - Plus a few extras I don’t have (Or want. J ). But between us, with home sharing, we have everything. Can we share playlists…
- On iTunes in the Home
- On iOS devices (I understand some songs may be missing)
Also:
- By the time I put apps on, and leave some space free for photos etc, My iTunes Library is way too big for my 16gb iPhone 4s, so I have manually unchecked a lot of my less listened to music.
- My 32gb iPod is a great size for me, for storing music and the odd video. I rarely use apps on it now that I have an iPhone.
- If I do get an iPad, it would basically be for apps. I’d want a bare minimum of my favorite music on it, just to get me through. It would however contain lots of photos, and some video.  In this way, I think a 16gb model would be plenty.
Is there a way to set up iTunes and my IOS devices so that they sync to the same library, but with content tailored for each device?
Also, with a setup like that, if a Playlist is missing a few songs because the source file isn’t on that device, will it still play the other songs?
Thanks SO much.

- My PC Library contains all the music and Apps I had up until that change. (This is before I worked out how to use iCloud.)
How did you work this out with iCloud? It has little to do with iTunes.
1 - playlists. On the old computer, open iTunes. File > Library > Export playlist.
This will export a file. Copy this file to the new computer then File > Library > Import playlist. It will duplicate playlists (not files) if they are present in both libraries but you can simply delete the playlist you don't want.
2 - Doing 1 above will add the playlists to the Mac.
3 - To get the playlist from the Mac to the PC, do as 1 above but in reverse.
Or if you want it an exact duplicate...
Delete /Music/iTunes/ folder on the PC.
Copy the entire /Music/iTunes/ folder on the Mac to /Music/ on the PC.
This is all you need to do.
and keep it all up to date with iCloud
Do you mean iTunes Match ($24.99 a year)?

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