Probably not worth it. By Valve's measure [0], 0.84% of Steam users are on Linux. They have made the investment into Linux support toward the promotion of their own Linux based hardware. Apple has no such incentive.

Does iTunes not run well enough in Wine [1]?

I say this all as a frequent user of Steam on Linux and a nonuser of iTunes.

[0] - http://store.steampowered.com/hwsurvey

[1] - https://appdb.winehq.org/objectManager.php?sClass=applicatio...

I haven't synced my iPhone with iTunes in around 3 years. The only cost is iTunes Match (£25 per year) which puts all of my music in the cloud and available to my device.