This needs to be either wifi or RF (and looking for recommendations for this too). I've tried IR and bluetooth options in the past and they just don't work reliably enough. There's nothing worse than dropping audio packets just as the denouement approaches. I think this is probably the quality of the bluetooth transmitter though - I've got a reasonably good of bluetooth headphones that work perfectly with my notebook, but are just too erratic with the TV (and my phone).
I've also considered the Logitech-type RF options. The current setup has a HTPC so it would be fine if everything was routed through the PC, but we do have some other devices too so have rejected that for now.
I've also looked at dedicated wireless headsets, which are an option, but they seem relatively pricey for what they do (I'd probably just buy a Roku unit instead).
Ideally this needs to support two headsets. A simply Y-splitter will deal with this if we go down the couch option, but would probably add quite a bit for other options.
Using a phone as a wireless receiver might be an option, but I'd probably prefer something dedicated.
Any suggestions welcome.