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Interesting experiment; Steven please do update us with regard to his observations once his experiment ends. By the way I am not experimenting but I haven't used Gmail / Google in ages, instead I've been using Hotmail/Yahoo Mail (for about 90% of my time/mails) + Bing, and it is pretty hard to differentiate between them. In fact, I'll give MS a huge plus for WLM App. Beside, I just noticed Owen agrees with one observation which I already have i.e. WP7 have the best/minimalist interfrace (and being an Android user i.e. GT-i9000 set, I will add it feels like iOS's cheap copy / slow / crash prone)
Bing and Google come pretty close for quick searches, and I don't care that much about advanced functionality on Google Docs or cloud-based Office as long as those serve the purpose of letting me share a file with a group. However on the email front, I find Gmail to be way superior to Hotmail. In fact, I'd say Hotmail even at this stage is an insult of what hassle-free webmail should be.
Too lazy to find my password here, but I have to say, I can't find anything different between the search engines, the big thing that I noticed is Bing Translator and Google Translate don't really compare, Bing is far superior. As far as Gmail being a "hassle-free" webmail, I disagree. They require users to have a phone number handy to activate an account, not hassle-free at all. Just wish Hotmail natively integrated chat other than Live...come on down AIM...