I think it depends on what type of area you live in as to whether or not you should allow your Ragdoll out, to be honest if the area is safe enough for your moggie Jeremy then it's safe enough for Rolo too.
My two cats were indoor only for the first year of their lives with no issues, we have since moved to a house with a garden suitable for catproofing and although I live in a 'nice' area in a very quiet cul-de-sac the main 70 mile an hour road is far too close to allow my boys free reign so I've catproofed the garden using a Secur-a-cat cat proof fencing kit, basically inverted netting attached to the top of the fence so they can enjoy going outside with none of the dangers. In my opinion catproofing gives he best of both worlds when the situation dictates they can't roam freely for whatever reason.