Two channels out of a single box is not an option.
So if that is not a problem then just hook up a video sender to the Sky box. If you are not using the VCR SCART on the Sky box then that would be an option.
The main problems with Video Senders are...
They don't much like transmitting through walls and floors. So OK if the bedroom is above the living room but might be an issue if the Sky box is in the basement and the bedroom is in the attic on the opposite side of the house!
If you or your neighbours have wireless networking on your broadband, or your neighbours have video senders themselves you may struggle to find a completely interference free channel.
Though if you do have a wireless router and can get a decent signal on a laptop in the bedroom (assuming the router is in the same room as the Sky box) then chances are a Video Sender will work as well - as long as a free channel exists obviously.