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I prefer Windows Live Hotmail. One of the reasons I prefer it is because I can make e-mail aliases for my main address to handle spam and protect against possible junk mail. Also, unlike Gmail's alias option, The alias doesn't have to be related to the root address. Thus, it's harder for spam businesses to target your aliases. :)
I use mail. The only email I check is my Mobile Me / iCloud address (maaaaaybe my gmail every now than then), even though I have soooo many email accounts.
I'm split between using both Hotmail (now Outlook) and GMail, with no real preference to one over the other. My Hotmail address continues to be my main account, though, as it's the same e-mail address that I've had for 8 1/2 years, and basically anything I've signed up for in the past is linked to that rather than my GMail.
Gmail, used to have lots of hotmail/Windows Live accounts for making game accounts, as they are easy to make then, but now... I only use my Gmail account.
I mostly use hotmail purely because that was my original email account. I've signed up to way to many sites using that email to change it now, so I just put up with it.
All of my new email addreses are done through gmail though. I prefer the layout of it all and the integration with the rest of Google's products.
I have a bunch of different addresses for multiple different reasons. So instead I just throw them all into Thunderbird. If I'm forced to pick though: Gmail due to how straightforward it is.
I use Sparrow for my Gmail and custom email accounts simply because I'm a sucker for good user interfaces. I use email more than instant messengers nowadays and actually it's been like that for the past three or so years so having a good email client is crucial. It's a shame that the team behind Sparrow left to work for Google. There will be more feature updates done to the client and if there will be any updates it'll be security fixes.
Sparrow is still useable, no doubt, but sooner or later it'll have to be replaced. I'm patiently waiting for Unibox, .Mail, and perhaps the native Mac client of Mail Pilot.