Transitions, Transitions!

I would think the bedroom change would be the easiest thing. Then you can try the big boy bed but he might be more apt to climb out without the crib sides there (I read somewhere that before the age of 3, it's difficult for many kids to recognize "imaginary" barriers, such as the edge of a bed, which is why it's harder for them to stay put). As far as potty training, that's really up to him, and if he's physically and emotionally ready - if he's not showing any interest or awareness of going pee or poop or of sitting on or using the potty, you are not going to get too far. Keep in mind too that many potty-trained kids regress when a new baby arrives, so unless he is showing some serious potty-training readiness signs, I don't think I would even attempt it - you would be better off waiting until he's older, more open to potty-training, and he's had more time to get used to baby being in his life.

You can control 1 and 2, but not 3. 3 is dependent on his body. You can encourage and help with #3, but don't turn it into a battle. It's not worth it. And you're going to have to let go of some of the planning stuff :) He's his own little person, so take a deep breath and let his body timetable go. The bedroom stuff is deal-able. Congrats!

I would put him in his crib in the new bedroom and not rush to put him in
a bed. As long as he is happy in his crib let him be. Would not even
think about potty training him unless he is ready. He will let you know if he
is. However, even if he is, a new baby brings about regression. Try not
to over think all these things. You will find that all of your changes will
occur without drama if you just let them happen.

Put him in the crib in the new bedroom.
Then after Christmas put him in his new bed.
Hide the crib in the basement until baby needs it, like next July when it outgrows the bassinet.

POtty training I can't help you with. He will give you signs when he is ready and if you force it he will just dig his heels in and make it worse.

I talked abut the babies and we sang songs to them. We named two early so the kids knew who they were talking about.

Start having a babysitter come over now so when baby comes the older one is used to her. I had a M.'s helper with number 4 and my daughter has been one for my neighbor.

Move him to his new room now and keep him in his crib until he adjusts. IF you need him to be in a big boy bed before your new child is born wait until he's been in the new room a couple of months, say mid January, and put the mattress that will go on the bed on the floor. After he's adjusted to sleeping on the mattress put up the bed. If you can do all this at least 3 months before your new baby arrives he should be adjusted by that time and not associate the move to the new room and bed with his new sibling.

As far as potty training, timing is up to HIM. You can have a potty out for him to see and play with now, buy books and DVD's, talk to him about using it and allow him to see you and his daddy using the bathroom. But until HE is ready to sit and go, can understand the feelings of needing to go, is uncomfortable in wet or poopie diapers, and can tell you he needs to go or can go on his own it will be an experience in futility. This isn't to say he won't be trained by next June, just saying it may not happen according to your plan ; ) If you have the energy and patience you can start now, but it may be beneficial for all to wait until a few months after the birth of your 2nd child, as potty regression is fairly common after the arrival of a new sibling.
The following sites may help:

http://www.parentingscience.com/toilet-training-readiness... ~ readiness
http://www.parentingscience.com/potty-training-techniques... ~ methods
http://www.parenting.com/article/potty-training-guide

Personally I'd leave hi alone in his crib. Borrow another O. if you have to.
He may be ready to be potty trained--maybe not--that will put you at 2ish...many boys aren't trained til closer to 3.
If he's not *ready* it's not going to happen...no matter how much you want it to happen!
Good luck!

We moved my son to a new room. My husband built book cases that went around the window, let my son "help", and we told him that it was his new big boy bedroom. My SIL gave me dinosaur themed sheets and a bed coverlet, and I got some dinosaur posters laminated to put over the bed. We bought a new twin bed mattress and got the bed all set up. Last thing was all the toys and books on the shelves.

We played in that room at night time, but put him in his crib. Then it came time for vacation. He slept on the bed during naps, and in the playpack at night. When we got home, he wouldn't go back in the crib. So we moved him into his new room! He never was interested in going back into the nursery again, and he didn't feel any resentment at all for his little brother being in his old crib.

I will say that for the first 6 weeks, I had both of my kids in a small bassinet in my bedroom (I did not co-sleep). So if you have trouble moving your son by the time the baby is born, you might consider doing that. I moved my babies to their real crib at 6 weeks because that is when they weighed enough to sleep through the night.

Hope this helps,
Dawn