Here's the message dialog shown after wake up:
Internet Connect You have been disconnected form PPTP server because the network configuration has changed.
Yes, sometimes it reconnects by itself. But don't think it's because of VPN server-side timeout. When you're in sleep for short enough time, the Wireless connection is not fully killed off and reconnects instantly, and VPN connection is not lost! In longer sleep periods it takes longer time to reconnect wireless, that's when VPN connection drops. But reconnection of wireless takes 2-5 seconds, it's not that big problem OSX shouldn't work around easily.
So the problem is OSX should detect that network connection was interrupted by sleep and it's reconnecting. Restoring the connection usually takes 2-5 seconds. So why it show up this message when OSX can reconnect just fine?
This message is shown about 10-20 seconds after wake up. By that time wireless connection is already re-established and OSX should retry VPN connection automatically.