I'm STILL struggling with this, and there STILL doesn't seem to be a solution.
- SuperSync requires that the SS app be running on both computers, and you need to manually go through the sync process. Also, unless you haven to have a static IP, you can ONLY do this when both computers are on the same LAN. It won't do it automatically, or even at a preset interval without a LOT of AppleScripting, and if one computer is at home and you're on the road, forget it.
- iCloud is expensive, impossible unless one is willing to update to the newest OS right away every time (nope!) and seems to only work with purchased items (from what I have read; I am not running ElCapitan, so I can't say personally). iTunes match is also pricey, and seems to have issues with non-Apple content as well.
- Dropbox only sort of works. I have enough space to do it (I pay for DB for other reasons anyway), but it freaks out about keeping it updated. If iTunes is open on both computers, it just creates a new library file, so within a couple weeks you can have dozens of "Conflicted copies," none of which reflect the most current state of either library.
Nevertheless, so far the best (and that's not saying much) solution I have is Dropbox, despite its flaws. IF there was a simple way to ensure that iTunes was never open on both machines at once, DB would be a perfect solution, if you don't mind the price, or if you have to have it for other reasons already.
There IS a way to use a freeware app and AppleScript to close iTunes on one computers when you open it on another machine, (instructions on LifeHacker here: http://lifehacker.com/5715126/how-to-sync-itunes-across-all-your-computers-with- dropbox ) but that will only work on the same LAN. Again, without a Static IP, if your desktop is at home, and you are at a coffee shop with your laptop, forget it.
At best, one could supplement that with a script that tells iTunes to quit on each machine when it goes to sleep, but if you use streaming or Home Sharing, or even a WiFi sound system, you'd have to fiddle with it so it wouldn't cut off when you're listening to music but not otherwise using the computer.....
And all of this is a ridiculous amount of fiddling to do something Apple should have built in to iTunes a decade ago....but I hope it's helpful.