I’ve got a rather substantial music collection but an iDevice that only holds a small fraction of that. I’ve been trying to use various playlists, smart and otherwise, to manage this situation but am so far pretty dissatisfied. The solution I want is close to the one Apple built for the iPod shuffle, the AutoFill feature, but it’s not available for non-shuffle pods. I’ve tried in vain to replicate this functionality with my nascent AppleScripting skills, to much swearing and ill effect.

But I’m betting someone out there knows how to do this. So, I’m putting up a bounty and a list of features in the hope that someone with greater code fu than I can solve his problem.

The bounty is $50, in the form of your choosing - paypal, Amazon gift card, iTunes, etc.

As for features, here goes.

• when I plug in my iPhone a random selection of albums should sync. Full albums not just random songs.

• there should be a setting for the maximum size in gigabytes that this random selection takes up.

• there should be a setting for the minimum rating of albums. It’d be really swell if this setting averaged an album rating across songs, such that a three song album with a 4 star song, a 3 three star song and a 2 star song averaged to a 3 star album. Averaging is a nice to have, not a requirement.

• ideally, the “randomness” of albums might be weighted towards highly rated albums that I haven’t listened to in a while. This might even be configurable. This is a nice to have, not a requirement.

• no need to weigh towards newly added albums since this is easy enough to accomplish with a separate “date added in the past 14 days” smart playlist.

• it should work on at least Mac OS X 10.5 and iTunes 7. I imagine AppleScript would be the mechanism of choice but Automator or some other solution that works on a stock install is fine. I don’t care about Windows, but if you’re the kind of masochist who enjoys cross platform programming, knock yourself out.

The deadline is my inbox by midnight June 1, at which time my favorite solution will win the bounty. If nothing is submitted by that time, the first solution submitted after June 1 that accomplishes the above wins.

You will retain full ownership of the code and can repackage, resell, or redistribute as you see fit. In fact, a cursory googling indicates that there’d probably be a small but worthwhile market for such a feature.