My last post is inaccurate. On Day 1 it didn't work exactly (except for the duplicate playcount). It missed some songs that were played on the iPhone between Sunday night and Monday evening. Mysteriously, iPhone doesn't show the songs as having been played (in my recently played list), although they may have been there before it "synced" with the cloud at some point Monday evening, but they definitely don't show in it now. It matched the library on my computer as of 8:50 pm. That's why I thought it was "working" save for the 2 playcounts for every one song played.
It's just very eerie. I know I listened to a new album entirely once, yet some of the songs show no plays and others show 2 plays in the library.
Day 2: Yesterday as of 9pm, it added just 2 songs played from the iPhone (although there more played then that, on the order of 10). All of the songs played from my Windows PC at work (which has always worked perfectly) were added the "cloud" and showed on all iTunes libraries and on my iPhone and iPad. When I used CloudScrob to scrobble my iPhone, it found songs played that weren't even reported as played in the playlists (because somehow those plays were lost), but even CloudScrob didn't see all of the song plays from Monday and Tuesday...
Today it hasn't updated...anything...at all played from the iPhone. I listened to some music downloaded from the cloud to the device while not on any data connection, to see what it would do. I also listened to songs while on data. Nothing has updated in my library at all. My SmartPlaylist on my device, however, is accurate for all of the plays today.
I'll be curious to see if it ever does update, and if so, if it misses any songs and if so, if those song plays disappear from my Recently Played smart playlist on my iPhone.
It really annoys me that this doesn't just work, even after 1+ years of existence of the service. I was really hopeful that I would have better success with the service after seeing these most recent posts.
It's really hard to discontinue using the service again when it really does fit my lifestyle much better. My library is just too large to fit on even the largest iPhone (first world problems i know) and to go back to manually managing it every day, and wired at this, is just a chore I'm not willing to put up with. If I go back to an Android device, smart playlists go away completely, so the compromise seems to be to just use it as it is, considering 95% of music is played from my iPhone anyway, so my smart playlists are always "accurate" there. THe last 3 months on an iPhone that I had to manually manage while plugged into iTunes just resulted in me not having the music I wanted to listen to any given time.
What a mess Apple.