I have many many email accounts. Let's see there's four Yahoo!, one Gmail, one hotmail, two personal site, one .mac, and one "work" account. Ten accounts! Is it necessary? I suppose because they all do a different and specialized task. I guess one of my Yahoo! accounts and Gmail are rather similar, but the rest all serve their own respective purpose. The number of accounts is of no concern (several are delivered to my Blackberry, which does a fantastic job separating) it's the lack of privacy that's offered which troubles me. Of course, when you use free webmail services you really can't expect too much privacy. Which is why I have subsequently installed GPG on my MBP and am using the Apple Mail plug-in for several of the accounts. True, you can't really have encryption unless your receiver as an encrypting/decrypting client but I can at least sign my mail to legitimize my actual act of sending. Come to think of it, I may abandon all of my webmail in its entirety and go to personal hosted accounts only, thus giving me more encryption control. Yes, I know about options such as Freenigma (for which I recently signed up), but your receiver still has to do work on his/her end by becoming a Freenigma user as well. And of course the lovely work email will always be what it is -- open and insecure. Not quite sure which way to go as of yet... need to think it through a bit more.