A disclaimer: I don't speak for Google, and my views aren't those of my employer, and if I was smart I wouldn't say anything, but I figure what the hell.
What the hell is up with this whole GMail is bad thing? I know that Orlowski is giggling with glee as the rest of the world joins him with his idiot Google bashing, and I was amused as always by the "OHMYGOD" of Google Watch (links left off since I'm certainly not helping their pagerank), but so many others have also jumped on this bandwagon... though, why should I be particularly surprised that people with an axe to grind and an agenda would slant the story to benefit themselves.
The second major complaint is that GMail targets ads based on the contents of the email you are reading. Doing this is somehow worse than targeting ads based on all of your previous history with the website, which is how portals like Y! target ads. As near as I can tell, there is a creepiness factor here, possibly caused by the immediacy of the results. Somehow when you get ads for mortgage companies on a website, you don't relate it to the searches/page views you were previously doing on that site for mortgage information because that was days ago... yet if you and your SO are emailing back and forth about mortgages and home buying, having an ad on that page for mortgages and realtors is creepy? A can tell you at least one benefit: the immediacy means that we don't have to store anything about you to do it. Just take the information at hand in the email message and query the targeting servers. To show you targetted information the other way means storing everything you do and running gobs of data mining on all the information and then storing information about what each user is interested in and then using that informtaion to do ad targeting... that sounds worse to me.
There are other complaints that I've seen, of course. The above two at least have some sort of reasonableness to them, if you look at them cockeyed and out of context, but the people who complain that GMail is "every message you send, every message you receive in ONE PLACE, tagged and sorted and indexed...", I can't rightly figure out. So, because GMail provides more storage and better search, its more evil than any other mail provider? Who knew that small mail quotas and poor search were such defenders of privacy and freedom?
In any case, I would think that most of these issues come down to trust: do you trust Google or not? Has Google ever done anything that made you not trust them? Do you believe the Google "do no evil"? As someone on the inside who's seen the code and heard the open discussions amoung the employees, I do. But don't take my word for it, look at our record and make your own decision.
And I'll leave my pet peeve about how "private" email really is for another time.