Couple of Bluetooth Questions

My first question is regarding bluetooth headphones, Motorola S9 in particular. One of the main uses I intend for them is to listen to music outside in the winter (walking to class and snowboarding), meaning the iPod would be in a rather thick jacket (probably inside pocket), and the receiver would be under a hood and/or inside a collar. Would this kind of obstruction cause any infidelity in the wireless connection?

My second question is related: I have an iPod Video (w/o bluetooth) and iPod Touch (w/bluetooth). I would ideally like to be able to use bluetooth headphones with both iPods. In theory, I feel like I could buy a cheap USB female to female adapter, plug in the charger cable to the video, connect that at one end of the adapter and a bluetooth dongle at the other end to enable my iPod Video with bluetooth. Is this reasonable or would it not work?

Thanks.

Sorry, I clicked the wrong link when posting this. Can I get a moderator to move it to the iPod Hardware and Accessories forum?