In net-im/gaim-2.0.0_beta5-r2 (MSN protocol), when an IM is sent to a recipient, that message isn't displayed in the window, until the recipient sends a message back. Then the IM is displayed followed by the new message from the other person.
Not to sound mean, but could you perhaps launch gaim from a terminal and show me the output from when you try to send a message over msn, oh and also emerge --info would be nice to.
Can you reproduce with net-im/pidgin?