From my experience, the iPad 1 WiFi edition will not allow for using a bluetooth headset (or headphones) in conjunction with a VoIP application like Skype. Not sure if iPad 2 has been changed or not, though.
I've got a pair of Sony DR-BT50 headphones which include a microphone for doing HFP (Hands Free Profile) and it has never worked for me - I can only listen to the stereo audio coming from the iPod player, movies, and games. I have only ever been able to use a wired headset for Skyping. What's interesting is that these same Sony DR-BT50 headphones work perfectly with my Motorola Droid phone for calls and audio listening.
This forum post seems to answer pretty well:
And here is the actual Apple support page detailing the various Bluetooth Profiles supported by their mobile iDevices:
Message was edited by: DJSsupp
There is no solution that works to talk on Skype via Bluetooth. I have called and tested every which way for iPad.
I have 2 Bluetooth headsets - they work beautifully on Mac, Winblows and Linux for Skype calls.
They also work perfect for listening to music, on the iPad - I even hear incoming Skype chat and phone call alerts.
Click answer and the audio goes to the built in mic/speaker on the iPad.
I checked with Skype, Truphone, Fring - all have told me that Bluetooth is enabled in their code.
Sad that Apple could not add one line of code in iOS5 in order to enable audio and mic for the actual calls...
Skype broadcast their new iPad app. all over the web "now,with Bluetooth capability" - not one developer actually paired a device to see if it worked? Also sad...
Wired headsets do work. I wish the iOS5 video were to show these people - and Siri getting tangled as the fight to plug in - like I do all day.
This is not a problem with the type of Bluetooth headset - it's a code problem in iOS. TIRED of getting tangled up in wires, so that I don't sound like I am on a speakerphone.
If anyone has successfully made a skype call using Bluetooth - post - prove me wrong. As a recruiter, I read resumes and call people - I don't need an iPad for music. iPad = a Corvette with wooden wheels.
I had a wireless USB headset working but then Apple turned that off on their end too... 'the device you plugged in uses too much power' - camera connection kit - in the trash.