How about using the Mayaflash Dolphinbar?

It always automatically connects when the board is turned on and just costs 20 bucks :)

That's still just a Bluetooth receiver so it would have similar issues with paring

No, it's specifically made to emulate a real Wii. When you turn the WiiMote or Board on you don't have to sync it anymore, it'll act like a real Wii at that point and you still have all the sensors, buttons etc. available