This has been a question for a while now but today I came across an interesting article on Chicago tribune talking about the same dilemma I have. (Article was talking abt AOL, but my conundrum was with hotmail).
Well Hotmail is not as old school as AOL(at least they are keeping up with the trend) but not as trendy as Gmail is.
Having said that for me Hotmail, still works fine and it is my primary. Yes I have a gmail account too, but it’s mainly secondary for my geek and fun stuff. For everything important, Hotmail is treating me just right.
Plus, even if I send a massive email to all my hotmail contact(which I only talk to like 20 out of 200) I bet they’ll not even take the time to update my contact info. So what’s the point.
Don’t take me wrong, I love Gmail and it’s capabilities, but I don’t think it’s really neccessary to completely transform to Gmail.
(As a matter of fact I still have a yahoo account which i log in like 2 times months, lol)
In conclusion, I think just use the whatever works for you and sticking with it is the best option, coz if you keep changing your email address, you, your self is harming the identity of your own email.