Now having switched to the iPhone 3GS for more than half a year, I found some more aspects to compare them. A smartphone has to elimiate the need for a separate iPod, which I use it mostly for Podcasts and Audiobooks.
Though I buy some Audibooks on CD, sometimes I download them from Audible like I did two weeks ago to get Dan Brown's latest Lost Symbol in an unabridged edition. The Audible integration is perfect with the iPhone, 5 points for that. But I found out that there is no officially way to get Audible books on S60 6th Edition devices. OK, one could burn the whole book on CD and re-rip it, but eg. the Lost Symbol contains of more than a dozen CD's, which adds the costs of the CD's and lots of work. At least, there is a way, but I would not want to do that. Only one Point for S60 5th for the option via CD-reripping.
There is an Audible player for S60 3rd Ed. called AudibleAir which offers over-the-air (OTA) downloads. But this is not available for 5th Ed right now, while we are hoping to see Symbian^3 next month. Even on my E51, I did not manage to get AudibleAir to do something useful. The installation is awkward. It is a Windows executable, which installs the software on a SD-Card, so it will be installed when the card is inserted into the device. But this did not work for me. On Audibles help pages, I found the jar-file ... AudibleAir is a Java application. This means, it is constantly asking for permissions several times. At least I manage to login to my Audible Account and browse my library. The app could be switched to German, but failed to display German Umlauts, showing some funny special characters instead. In the End, the application failed to download any of my audio books, but giving me some communication error instead.
So adding to my comparison chart:
iPhone: 5, 5800: 1
iPhone: 101, 5800: 94