My mac/iphone mail is receiving but not sending

First my mac wouldn't send out emails, saying "Hotmail (offline)".  I've tried re-entering my email and passwords many times and nothing seems to work.  Now or some reason this is also happening on my iPhone 5, but instead it says to enter my Apple ID password then once I do it says that my email username or password is wrong when I have used exactly that to sign onto my web email.  Any thoughts?

I started having many problems, including this one, as soon as I installed the 10.5.6 upgrade. Only one of my IMAP accounts is having problems (Gmail is fine so far), but the account is working ok when I access it via Thunderbird. I tried almost of the solutions posted above. I also installed the 10.5.6 Mail patch. All the fixes worked briefly, but after a couple days the problem returns. It must be a problem with my OS account because I can access the IMAP account via my laptop with no problems. That was the one fix you mentioned that I didnt try because I dont want to have update all the settings associated with the current user, and since I would have to restore everything, does it seem more reasonable to just do a clean install of the OS?
So my question is, do I give up on Mail on this machine? Or do I have to do something like a system wipe?
Thanks

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