Weird outgoing mail issues after snow leopard upgrade

After upgrading to snow leopard a couple of weeks ago (then immediately to 10.6.5), I have been having trouble sending mail from my work machine on one account. After reading these forums and trying several solutions (listed below), the thing which seemed to work for me was deleting the outgoing mail server entry in the preferences pane and re-entering the information. However, this solution does not always work for me, and is only temporary; after some amount of time (variable? on the order of minutes?) the problem recurs.
If I open connection doctor the server in question displays a "Connecting to server..." message for a long time (minutes) and then "Could not connect to this SMTP server. Check your network connection and that you...". I get this behavior even just after resetting the smtp server, while I am successfully sending test emails.
As with others here, the same account works fine on other machines.
Things I have tried, on my own or based on advice read in the forums:
1) specifying the port for the server in advanced settings
2) Deleting and re-adding both the smtp server and the imap account
3) Setting mobileme to manual sync
4) "cd /var/log;touch mail.log;sudo chown root:admin mail.log; sudo chgrp 644 mail.log" (which doesn't produce any logs for me).
Any help would be appreciated.

I for got to add
5) repair permissions in disk utility
6) reboot

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