I would LOVE a kitty like that and I am heartbroken if mine do not sleep with me in the bed! I think you are LUCKY to have one like Brodie. (Chester slept on my pillow until he got to big to get there anymore)

You have to understand, he is use to having someone to snuggle up to, the warmth and closeness of someone being there so having to be alone, it is understandable that he cries and cries.

Once he and Josie become friends, he can sleep and cuddle with her and that will help a lot. Can you put a heating pad in his bed with a stuffed animal and try that for warmth and cuddeling until he can sleep with Josie?

Don't worry about rolling over on him, they are quick to get out of spots like that. I have slept with every kitten I have ever had and never had a problem...

One cat I had, came from a pound and she HAD to sleep on my pillow where she could feel me breathing on her all night. I LOVED it!