There seems to be a major flaw in the implementation of the backgrounding in Skype, either that or it's just me?
If you log into Skype while you have WiFi coverage, if you then move out of WiFi Skype stops working, it doesn't switch over to 3G automatically. You then don't receive any messages or calls.
Perhaps this is because they're not using push notifications, as I've not seen other apps do this?
This is not a flaw. It works as designed
You realize, that while on WiFi you have a completely different IP adress than via 3G? As soon as the phone loses wifi connectivity it gets a whole new ip adress from your cellular provider and all connections get aborted.
The only reason you haven't noticed any side effects of this behaviour is that you haven't been streaming any audio (or doing VOIP) while changing networks. All other data is packet based session data and nobody cares which ip adress it came from.