IMessages Frequently Fail to Send from OSX

I am having a problem with iMessages through Messages on OSX Mountain Lion failing to send, or messages not being received.  Typically this occurs after I have not sent/received a message to a contact for a period of time, and resending it will suceed and all future messages will succeed for a period of time.  The period of time ranges from minutes to tens of minutes.  At one time it got so bad that no messages would be sent/received correctly.
Messages works perfectly on my iPhone.  The problem cropped up very suddenly after I replaced my modem/router.  However, it does not seem to be specifically related to the connection as the problem occurs on any network/ISP I have been on with my laptop.  The iPhone works perfect over cellular or over WiFi, including on my home network.
What I have tried so far:
1. Re-syncing Messages on OSX and iPhone by signing out on each, and signing back in (and allowing it to pop up the confimration messages that a new device is signed in).
2. Deleting a bunch of plists (anything with messages or im in it).
3. Deleting my keychain.
Doing these can improve it for a time.  Maybe it will work perfect for an hour before it starts to have issues again.
Does anyone have any further advice?  If not I should probably contact apple directly.
Thank you for your suggestions.

HI,
I did cross my mind that a New router might have a shorter period before closing what it thinks are unused ports if set to use UPnP.
For example UPnP will basically allow the app on the computer to tell the router which ports to open.
In Messages with an AIM or Jabber account you can Video chats from the App.
This means sending a Visible invite on Port 5678 and potentially connecting on port 16402
Various routers have a default time that these port remain open after the last data passed.
The AIM logins as well as the Jabber and Yahoo ones are "Always ON" connections which allows the Buddy lists to update virtually instantly when Buddy goes Off Line, Changes their Status or Message or their Buddy Pic.
It is less clear about the iMessages account as there is not indicator within the app to say whether you are connected to the server or not.
Having said that you report that an iPhone is having no trouble using the same router.
The info I have is that the iOS version and the Mac version do in fact use the same ports to login and send Text.
It would seem the iOS does a better job of keeping the app connected when it needs to be as well as extending the battery life as long as possible compared to the Laptop.
I think this is related to the way the OS works rather than a direct setting that you might change  (Although System Preferences > Energy Saver might be a starting place).
I can see where thr problem might be but have no concrete suggestions as to what steps to take next.
I feel it is going to be a call to Apple.
8:30 PM      Thursday; June 27, 2013
  iMac 2.5Ghz 5i 2011 (Mountain Lion 10.8.4)
 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

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