How To: A New Album Every Time You Sync Your iPhone

When I bought my iPhone 4S, I opted for the 16GB model, mostly because I sync my phone a couple times a week clearing photos, videos and other data. I underestimated how much data 1080 HD video takes up and I would suggest future buyers to go for the 32GB upgrade. The other major data source on the phone is of course music.
I consider myself a bit of a music hound, getting dozens of new albums a month across all genres. I then throw them into my 2012 playlist and each time I sync my phone it automatically pulls in the new music and deletes anything I’ve either moved to my permanent collection or deleted.
This usually satisfies my musical appetite, but every now and then I want to listen to older albums from my 200GB collection. I try and keep a “classic albums” playlist together, but it gets stale quickly and I rarely listen to it, taking up valuable space of my puny 16GB.
The Goal: Every time I sync my iPhone, I want to remove albums that if I’ve listened to since the last sync and replace them with new albums that I haven’t listened to in over a week.
The way to do this is using smart playlists, which after you start using, opens up tons of possibilities that you would have never thought possible. Hat tip to the Apple engineering team for an underused, but very powerful feature.
Step 1: Change the way iTunes “randomizes” content, instead of choosing random songs, choose random albums. Simply click Controls -> Shuffle -> By Albums

Step 2: Next create a smart playlist. File -> New Smart Playlist

Step 3: Now the fun begins. Smart lists are based on adding filters and I created 4, but feel free to add more to further narrow your content set. The ones I created are: 1) Filtering out the audiobooks 2) Removing albums if played in the 7 days or 3) Skipped in the last 14 days and, finally, here’s the tricky part: 4) In order to include the largest set of content possible, 4) Album contains ” “. Important to note that you need to have the space there, as the query can’t accept blank entries. So, basically a space means to include all albums (besides the above criteria).
The last few check boxes are to limit to 1GB so that we don’t overload the iPhone (you can use as much as you’d like) and finally live updating, which allows the playlist to update on it’s own.

Step 4: Last step is to include the smart playlist in your iPhone sycing, and you’re done!

**I’ve noticed that the play count is only updated if a song is played till the end for some reason. Further, also seeing some problems updating the play count if using a bluetooth headset. Let me know if you see these issues as well.
Image Credit: Deadmau5 & ClubDrive.org