I did a 5 year investment, and we're about 1.5 years into it. My complaints are:
iPhoto albums are single user. Attempting to put the iPhoto DB on a network drive and sharing it to have a single consolidated 'family' album is an exercise in futility (even if you access it one-at-a-time).
Apple's groupware works fabulously with iCloud, and not so fabulously with google's offerings... which we had prior to converting. This has caused a few headaches.
Apple Maps occasionally get things hilariously/tragically/seriously wrong.
Safari's adblocking and privacy extensions are not as mature/robust as FFox.
Developers think they can charge money for stupid/mundane shit (OCR'ing a scanned PDF document for example). Linux VM's FTW!
Overall, It's been a nice experience. I've lost no love for linux in the process, and continue using and contributing to the FOSS ecosystem to the best of my ability.