Is it a good idea to document this on YouTube or not?

its not in violation of your probation. it was said that you couldnt get in any trouble. how is making a vid going to get you in trouble? you might want to check up on your probation officer if its ok for you to make a vid. just to be on the safe side and to make sure that there is no rule to it. it would be interesting to see how you two deal with being chained together. :)