Suddenly mail spins forever on send/receive

Hello Community...
I am trying to help my father troubleshoot his Mail program from 5k miles away! Before I lead him into remote desktop, I thought I would try here and see if someone has any ideas of what to do for him. So thanks in advance!
The situation:
He is running a 24" iMac with the 10.5.8 and Mail 3.6, I believe.
He has a .mac email account which is setup in Mail and was working trouble free until a few days ago.
His last message is from Nov. 29 but now the little icon just spins and spins never sending or retrieving anything.
He is able to access the account from his iPhone and also by signing in online at me.com
The internet connection is fine, as we were trying to solve it over skype.
Troubleshooting tried so far:
Check account setup - all OK
use connection doctor - all green
move com.apple.mail.plist to desktop and restart mail - no difference
repair disk permissions/restart - no difference
check for automatic updates that may have affected mail - not sure. There was one on Nov. 28 for HP printer driver and iPhoto. Because he has mail from the 29th it doesn't seem a likely culprit.
If anyone has any ideas of where to look next, I would appreciate it!

I am having the exact problem on my MacBook Pro, but not on my iMac. I tried deleting the cache.db file and it didn't change anything. Any other ideas out there? I am running Leopard 10.5.8 and I have run all the latest software updates.

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Hi! I think Apple Server update (PPC) 10.4.9 has screwed up my mail settings...and hence i did a clean install of OS 10.4 (Tiger) with stock software and nothing else.
I added in the same configurations but the mail server just will not receive or send out any mails via smtp.
Here's the postconf -n output:
mail:~ colordoc$ postconf -n
command_directory = /usr/sbin
config_directory = /etc/postfix
content_filter = smtp-amavis:[127.0.0.1]:10024
daemon_directory = /usr/libexec/postfix
debugpeerlevel = 2
enableserveroptions = yes
html_directory = no
inet_interfaces = all
mail_owner = postfix
mailboxsizelimit = 0
mailbox_transport = cyrus
mailq_path = /usr/bin/mailq
manpage_directory = /usr/share/man
messagesizelimit = 0
mydomain = colordoc.com.sg
mydomain_fallback = localhost
myhostname = mail.colordoc.com.sg
mynetworks_style = host
newaliases_path = /usr/bin/newaliases
queue_directory = /private/var/spool/postfix
readme_directory = /usr/share/doc/postfix
sample_directory = /usr/share/doc/postfix/examples
sendmail_path = /usr/sbin/sendmail
setgid_group = postdrop
smtpdpw_server_securityoptions = plain,login
smtpdrecipientrestrictions = permitsasl_authenticated,permit_mynetworks,reject_unauthdestination,permit
smtpdsasl_authenable = yes
smtpdtls_keyfile =
smtpduse_pwserver = yes
unknownlocal_recipient_rejectcode = 550
And here's part of the mail.log:
Mar 19 09:53:23 mail postfix/smtpd[339]: connect from localhost[127.0.0.1]
Mar 19 09:53:23 mail postfix/smtpd[339]: E0D7E1E018: client=localhost[127.0.0.1]
Mar 19 09:53:24 mail postfix/cleanup[346]: E0D7E1E018: message-id=<[email protected]>
Mar 19 09:53:24 mail postfix/qmgr[56]: E0D7E1E018: from=<[email protected]>, size=742, nrcpt=1 (queue active)
Mar 19 09:53:24 mail postfix/smtpd[339]: disconnect from localhost[127.0.0.1]
Mar 19 09:53:26 mail postfix/smtpd[349]: connect from localhost[127.0.0.1]
Mar 19 09:53:26 mail postfix/smtpd[349]: 868861E03D: client=localhost[127.0.0.1]
Mar 19 09:53:26 mail postfix/cleanup[346]: 868861E03D: message-id=<[email protected]>
Mar 19 09:53:26 mail postfix/qmgr[56]: 868861E03D: from=<[email protected]>, size=1137, nrcpt=1 (queue active)
Mar 19 09:53:26 mail postfix/smtpd[349]: disconnect from localhost[127.0.0.1]
Mar 19 09:53:26 mail postfix/smtp[347]: E0D7E1E018: to=<[email protected]>, relay=127.0.0.1[127.0.0.1], delay=3, status=sent (250 2.6.0 Ok, id=00225-01, from MTA: 250 Ok: queued as 868861E03D)
Mar 19 09:53:26 mail postfix/qmgr[56]: E0D7E1E018: removed
Mar 19 09:53:31 mail postfix/smtp[350]: 868861E03D: to=<[email protected]>, relay=mx2.hotmail.com[65.54.244.40], delay=5, status=sent (250 <[email protected]> Queued mail for delivery)
Mar 19 09:53:31 mail postfix/qmgr[56]: 868861E03D: removed
Did i forget any settings?
I would like to get the mail service up and running before I update to apple 10.4.x.
Please advise.
Thanks!

Please ignore the earlier post as I have made new progress.
The server is up and running...
It's a stock 10.4 Tiger server without any updates installed...
I've madesome changes..and amazingly the system came back alive...
I'm able to receive emails and send out emails but it's troubling me as i still see mails been deleted from queue in the mail.log
Here's the mail postconf -n
command_directory = /usr/sbin
config_directory = /etc/postfix
content_filter =
daemon_directory = /usr/libexec/postfix
debugpeerlevel = 2
enableserveroptions = yes
html_directory = no
inet_interfaces = all
mail_owner = postfix
mailboxsizelimit = 0
mailbox_transport = cyrus
mailq_path = /usr/bin/mailq
manpage_directory = /usr/share/man
messagesizelimit = 0
mydestination = $myhostname,localhost.$mydomain,localhost,$mydomain,mail.$mydomain,www.$mydomai n,colordoc.com.sg
mydomain = colordoc.com.sg
mydomain_fallback = localhost
myhostname = mail.colordoc.com.sg
mynetworks = 127.0.0.1,202.73.35.131,202.73.35.142
mynetworks_style = host
myorigin = $mydomain
newaliases_path = /usr/bin/newaliases
queue_directory = /private/var/spool/postfix
readme_directory = /usr/share/doc/postfix
relay_domains = $mydestination
relayhost =
sample_directory = /usr/share/doc/postfix/examples
sendmail_path = /usr/sbin/sendmail
setgid_group = postdrop
smtpdclientrestrictions = permit_mynetworks permit
smtpdpw_server_securityoptions = login,plain
smtpdrecipientrestrictions = permitmynetworks,reject_unauthdestination,permit
smtpdsasl_authenable = yes
smtpdtls_keyfile =
smtpduse_pwserver = yes
unknownlocal_recipient_rejectcode = 550
and here's the mail.log:
Mar 19 13:03:04 mail postfix/smtpd[986]: connect from unknown[202.73.35.131]
Mar 19 13:03:04 mail postfix/smtpd[986]: warning: unknown[202.73.35.131]: SASL LOGIN authentication failed
Mar 19 13:03:04 mail postfix/smtpd[986]: disconnect from unknown[202.73.35.131]
Mar 19 13:03:27 mail postfix/smtpd[986]: connect from localhost[127.0.0.1]
Mar 19 13:03:28 mail postfix/smtpd[986]: 1603122407: client=localhost[127.0.0.1]
Mar 19 13:03:28 mail postfix/cleanup[1139]: 1603122407: message-id=<[email protected]>
Mar 19 13:03:28 mail postfix/qmgr[747]: 1603122407: from=<[email protected]>, size=1240, nrcpt=1 (queue active)
Mar 19 13:03:28 mail postfix/smtpd[986]: disconnect from localhost[127.0.0.1]
Mar 19 13:03:31 mail postfix/smtp[1140]: 1603122407: to=<[email protected]>, relay=mx4.hotmail.com[65.54.245.104], delay=3, status=sent (250 <[email protected]> Queued mail for delivery)
Mar 19 13:03:31 mail postfix/qmgr[747]: 1603122407: removed
Mar 19 13:03:33 mail postfix/smtpd[986]: warning: 202.73.35.131: hostname brasbash.colordoc.com.sg verification failed: Host not found
Mar 19 13:03:33 mail postfix/smtpd[986]: connect from unknown[202.73.35.131]
Mar 19 13:03:33 mail postfix/smtpd[986]: warning: unknown[202.73.35.131]: SASL LOGIN authentication failed
Mar 19 13:03:33 mail postfix/smtpd[986]: disconnect from unknown[202.73.35.131]
Mar 19 13:04:40 mail postfix/smtpd[986]: warning: 202.73.35.131: hostname brasbash.colordoc.com.sg verification failed: Host not found
Mar 19 13:04:40 mail postfix/smtpd[986]: connect from unknown[202.73.35.131]
Mar 19 13:04:40 mail postfix/smtpd[986]: warning: unknown[202.73.35.131]: SASL LOGIN authentication failed
Mar 19 13:04:40 mail postfix/smtpd[986]: disconnect from unknown[202.73.35.131]
I think i'm having a false sense of security....
Can someone please point out if I have misconfigured the server...
Thanks!

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I had this problem since I got my Mac and 10.5.6. I've been using Thunderbird but would like to be able to use Mail for the integration with the rest of OS X, iLife. Thunderbird works as expected, sending and receiving.
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