Hi jennf.
i changed my DS to his room only 2 weeks ago (used to sleep in my room and in a bassinet too) but directly to his crib, the reason i did this, was because he doesn't wake up at night anymore, I didn't do it sooner, 'cause it was more comnfortable for me to have him next to me at nights when he woke up (not having to run to his room many times). But i guess if you change him to his room, you might as well put him in his crib, otherwise you'd have to change him AGAIN from the bassinet to his crib, and at that age for sure he wont notice that much the change.
Regarding the holding to sleep, have you tryied the pat-shush method, it will help him sleep independently... if you have any questions, i'm here to answer any way i can... the pat-shush worked wonders for my DS (it takes a while though) he doesn't need it anymore, and he can just sleep by placing him in his crib.