First problem (debatable, but I'm poking the bear:stirpot
: You're all using proprietary POS apple products. Yup, I said it, the Iphone sucks, get a Droid, they play nicely with Sync and are more capable pieces of tech. Apple products are bitchy, and Droid supports all of Sync's functions. Plus, Pandora radio via Sync > MP3 player any day of the week, so why use an Ipod?
Now, on to the useful stuff:
Second problem: Update your Sync system! Go to Syncmyride.com, get an account, fill in the data about your car, get a cheap USB thumb drive, follow the directions, a few trips out to the car....and bam, the latest and de-bugged version of Sync. I've done it quite a few times with my '10. Cleans up lots of the problems that early Sync versions had, and adds features that some may choose to use. I've been through 2 version updates and 3 status checks, all with no problems.
Third problem: As stated before, you must organize your music on your Ipod in a traditional Artist-Song-Album type format or Sync might trip over it. My wife's Droid had problems with her phone book working with voice command because of whatever mess of organization she had going on. We organized it, and now Sync is smooth.
Don't hate on Sync guys, because once you know how she likes it, she's a giver!