J.P.
I'm going to answer your bed question because I think our way worked out really well. I began transitioning my older son to a "big boy" bed just after his 2nd birthday because I was pregnant with our second and I needed that crib in 6 months! People said to wait until he is trying to crawl out of the crib, but I'm glad we took our time and did a slow transition BEFORE he was able to climb out of the crib. We had both the crib and a twin size bed with rails and fun sheets in the room. He was excited about the bed, but he kept getting out at naptime and bedtime. I would give him a warning, but if he got out again, he had to go in the crib. He began to see the bed as a privilege and getting out was not a problem after about a month. Also, we had plenty of time for him to revert back to wanting to sleep in the crib sometimes. So that by the time our baby was born, he was done with the crib and sleeping well in the bed!