Hi Jolly! I just adopted a baby girl that sounds a lot like your boy!

With the sleeping issue, it's not an issue at all! Kittys really enjoy being uncomfortable.. So if he gets cold or uncomfy on the wood, he will get up and lay in a more comfortable spot! My kitty sleeps in bed with me.. She right near me now running around on my bed.. Trying to hunt the pillows. :P

About the collar, like Raggs said, pet stores sell easy release collars designed especially so cats dont get caught and accidentally *Gulp* hang themselves! My kitty is an indoor cat, but I bought her one of these anyway! I'm sure if you ask a worker at your local pet shop, they'll be able to point them out right away, and even give you a recomendation. Most have a little elastic band that streches, or snaps (if they're really stuck) to let them get loose. Some just have an easy release clip.

Tell me if your kitty looks like mine! :P