After being tipped off by Sälli, I managed to take his iTuneMyWalkman application for a spin, and I have to admit that I am completely sold. Basically, iTMW can be used quite similarly to SyncTunes, but I particularly appreciate the clean user interface (slightly ahead of SyncTunes there), the supplied scripts for syncing automatically upon USB connection as well as the scripts installed directly to iTunes. Particularly the automatic syncing makes the whole process awfully close to ease of the ever-evasive iPod experience.
In order to start using iTMW with an S60 phone, you need a 3rd edition phone that supports the USB mass storage mode. Follow the instructions in the HOWTO for getting things working smoothly with USB. Next, download iTuneMyWalkman and install it by dragging it to your Applications folder.
When your phone is connected, fire up iTMW:

Before proceeding to the actual synchronisation, pay a visit to the Preferences pane and at least the General tab and set the path to the correct volume (the mounted memory card of your handset). Mine looks like this:

As far as I know, this is the only option you really need to specify at this stage. You can experiment with others later.
I dove right in and installed the scripts for iTunes as well as the folder actions from the main window. Based on brief testing, they work as advertised. The end effect is that once I plug my phone in, my playlist in iTunes is synchronised with the S60 phone completely transparently, without any further effort from my part.
Of course, the second best thing about iTMW is its unbeatable price (free), and the best thing is that it is open source, which means that if you do not like the way it works, you can improve it yourself. The application is built using AppleScript (which I consider to be the only read-only programming language in the world – doh!).
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