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Music sync wit iTunes

This is my 3rd Garmin device and I am more frustrated with Garmin than ever. If it wouldn't be for my workout history and the convenience of workout uploads through mobile app for Android I would kick it to the curb and try a different brand.

The reason I bought the Vivoactive was that I did not want to mess with iPods anymore and keep my running playlists on the device. 

First of all I had to go through  4 different "Garmin approved" bluetooth headsets before finding one that actual works (iFrogz) as expected. It is a narrow list but I can live with that.

But what  really gets me is that I can't get my playlists from iTunes on the device as set up on the PC. (Using iTunes for Windows) 

1. Garmin connect does not recognize all songs in a playlist. There are always some songs missing or left out. There is no rhyme or reason andno pattern on file types.
I tried all ACC playlist as well as mixed with "Purchased ACC files" and MP3's. It recognizes whatever it wants and it is all over the place.
And yes  - my iTunes and Garmin firmware as well as my Windows version are always up to date.

2. Some songs sync but they won't play on the device. The songs display on the device but will not play and I have to manually skip them. Again there is not pattern. They show in Garmin Connect as "on the device" but won't play. I tried a different cable which I had to buy to make sure, I tried several different USB Ports and I tried just one playlist - always the same issues.

I am looking for a polite word - but frankly this sucks and I am far away from my desired Outcome of getting rid of iTunes, as Apple has decide discontinue any iPod that is small enough to run with. I also don't want to run with my phone.

Thanks for letting me vent and if anybody has a suggestion how to fix the above I'd appreciate it. I already wasted hours on this and 1 or 2 more won't matter at this point.