My kids sleep with me, so I don't think you should feel pressure to move him to a bed because that's what other kids sleep in. We all just do what works for our family.
I like LS idea, and I would explain that he can get out, but it's important to try and stay in bed until morning (if that's what you want). Some people use a little light or alarm showing 7am so the child knows when it is morning time.
I think it could be beneficial for him to learn some responsibility and show he can stay in bed himself, but obviously only when you're all ready.
I think its fine to leave him in there if you are happy with it and your DS is also. My DD didn't start sleeping in the cot until she was 4 (she started having nightmares and as the cot was in our room would come and climb in and go to sleep) It got to the stage where it just become her bed. About a month ago I took it down and now she sleeps in her bed in her room 98% of the time. My sisters son slept very well in his cot until he was 3 when she put him in a big boy bed which he never stayed in and now at 6.5 he sleeps with her and has almost ever since she took the cot down despite multiple attemps over many months to ger him in his own bed again. Taking the side of sounds like a good idea and I know of people who take there kids to pick their bed themselves or some manchester to go on it to make it more exciting when they transition from cot to bed.
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