Mail mayhem

Help!
My Mail application is out of control.
1. I can receive but not send using my work email server. I've received all permissions from my work administrator, done first aid to my keychain, disk repaired, pinged, checked that my server is being used--every available online solution. How can I get it to work? It works in Entourage. I can RECEIVE mail from the server using mail. Help!
2. Mail is repeatedly asking me for passwords to my non .mac accounts, over and over again, even when I save it to the keychain.
3. Mail is creating duplicate emails in my drafts folder of emails I've successfully sent and show in my sent folder.
What is going on?
I appreciate anyone who can help me address any of these issues!
--Lazza

Dear travis,
Thanks for your response and sorry it took me a while to follow up.
1. Regarding the account where I can receive messages and not receive:
Connection doctor reaffirms my issue. All of my accounts show CONNECTION AND LOGIN TO SERVER SUCCEEDED except for one--the server "mail.permitplace.com" shows the following message: COULD NOT CONNECT TO THIS SMTP SERVER. CHECK YOUR NETWORK CONNECTION AND THAT YOU ENTERED THE CORRECT INFORMATION IN THE ACCOUNT PREFERENCES.
However the corresponding incoming mail server on that same email account, which is the SAME by the way, "mail.permitplace.com" shows CONNECTION AND LOGIN TO SERVER SUCCEEDED.
Suggestions?
2. Regarding the fact that I keep getting asked for passwords it should already know: I don't much understand KEYCHAIN but did try to run a repair and there are many duplicates for this account. I got rid of the duplicates but the problem persists. You wrote "Bear in mind that sending of emails can be done using SSL encryption or not and can use either port 25 or 587 depending on the system, so there are several ways to set this up." How would I know the proper way to set this up?
3. Regarding duplicate copies of emails I've sent successfully popping into my drafts folder, you wrote "The leftover items in the Drafts folder are indicative of network issues such that when Mail tries to clear the drafts folder (which likely is on an IMAP server of one account) the command fails for some reason." First of all, the accounts I have in addition to the .Mac account are set up as POP servers--not that i know what this means, but I don't see any IMAP accounts. Any remedies you suggest?
4. I have two new issues I forgot to address, one of which is similar to the third. Often when I receive new mail, if I look at it quickly and either delete it or move it to another mailbox folder, it will reappear in my inbox as a duplicate copy showing as unread.
5. If I get, say, 5 or more emails, they take a LONG time to download, particularly if there are attachments. I can click on them and they will show as BOLD/unread for a loooooong time.
I'm just spending WAY too much time dealing with these quirks. And the first issue I need to resolve for work or they'll make me use a PC. Should I just switch to Entourage?
I appreciate the help!
--Lazza

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