As for 2) I have the Nokia E61 and switch off GSM mode, when flying. This allows me to use it as MP3 player and I never had problems with any FA. None even asked.
For 1) I know, that SKYPE VoIP works on Laptops. So I don't see a reason, why a E60 in WLAN mode shouldn't work. But I wouldn't do it, because other pax may complain or may be concerned. (Yes, there are still people in the world, who believe, that mobile phones could cause crashes.
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