I think I know what might be going on..
On my Sony Xperia Z it has a battery saving app that will make the phones battery last longer (which is a default app on my device, which must say works great)
When the device is running on battery only (no mains power) it activates this power saving mode turning off my Wi-Fi etc.
When I wake up the phone, it will turn the Wi-Fi back on again. Even knowing it says I am connected to the Wi-Fi by the icon in the status bar up the top, it is still looking for a IP address from my router.
Looks like that even knowing the B4A-Bridge has given me a IP address, I think the device somehow remembers the last IP the router gave the device and shows that IP in the B4A-Bridge even before it fully connects to the router.
If I then try and connect the IDE says it can't ping my device as it's still connecting to the network.
If I then manually try and ping the IP sometimes it can't ping it and a few moments later it starts pinging as the device would of finally got the IP from the router even knowing it has given the same IP address.
If I am quick enough and open the settings app and view the network settings I found that the Wi-Fi is connect but it comes up saying it is trying to get a IP address, so that is basically how I knew that the device wasn't fully connected to the router/network.
Now when I close the app and IDE but leave the screen on so it doesn't activate the power saving mode on my phone and I re-open the IDE and app and connect again in the IDE it will connect first go.
This is most likely why my Samsung Galaxy S2 and Nexus7 are not getting these issues as it doesn't have this power saving feature enabled on them.
also have the same problem with 3.0, I hope this can be resolved...
Weird thing is it has only happened since version 3.00 as well but maybe I had the screen turned on for a longer time before I tried to connect using the older versions of the IDE and that is why it used to connect first go.
Maybe try this, before opening anything check and make sure your device has a IP address from the settings app then try and connect using the IDE and B4A-Bridge.