Re:- the second issue.
This seems to be a common compliant.
It seems to be worse if the Mac has been Off Line (Asleep or Shut down).
The iMessages server then tried to send the iMessages that it thinks the Mac has not had.
It does this like a speeded up chat but it is not Instant.
At the same time it will allow any current iMessages sent to you to arrive - even if they are in the same conversation - and they will get placed out of sync.
The Time Stamps do not appear to be used to place them in order.
Currently there is no Fix (other then reducing the issue by keeping the Mac On Line).
It can help if you turn the iPhone Off (Break with the server) and then On again or remove the Apple ID and then add it again.
Re:- the First Issue.
This maybe resolved by the actions above, particularly if you were sending to your own iPhone.
Please, if posting Logs, do not post any Log info after the line "Binary Images for iChat"
iMac 2.5Ghz 5i 2011 (Mountain Lion 10.8.2)
G4/1GhzDual MDD (Leopard 10.5.8)
MacBookPro 2Gb (Snow Leopard 10.6.8)
Mac OS X (10.6.8),
Couple of iPhones and an iPad
"Limit the Logs to the Bits above Binary Images." No, Seriously