Jeren just recently was moved out of his crib. He's 20 mos so I think it was last month I did it? He had already HAD his bunk beds in his room, the bottom being a FULL size as opposed to a twin, so the bigger bed makes it nice. I lay him perpendicular to the way he is supposed to go so he has more room to roll side to side, though he stays put pretty well anyways. He has a "guard rail" on the edge side and a body pillow at top (his right side but top if he were laying normal)and 2 big fat pillows along the wall side.
I transitioned his crib to the "toddler" bed and he napped in it 3 times and slept at night in it twice. He decided he wanted the bottom bunk after that. I just took the crib down a couple weeks ago, it's gone and he doesn't even care. I had to wait until I got large enough cardboard to wrap along the outer frame to block off the "ladder" of the bunk beds so he wouldn't crawl up to the top bunk...the crib was there blocking it until I could find something. The cardboard there doesn't look great but for right now it's function not fashion.
He loves his bed, did really well. Now, as a friend recommended, the crib is tucked away for a few months and then in a bit I can get it out for Audrey and set it up in HER room...I can better explain to him so he'll understand that it's BABY'S now, he's got a BIG BOY bed and it's not just going from his room to hers with an attachment still there with him.
SO, my hurry was a baby on the way and wanting to do it "right" But he was ready and willing also so that made it easy.
I kept a gate at his doorway for a short time but it was a PITA to hurdle over being prego so he just comes out when he's awake...I usually hear him first though. But he stays put when it's nap or bed time, during the night, doesn't keep getting up...he's usually pretty tuckered out and WANTS to rest.
Guess I got really lucky, lol.
I always expect the worst, I never give my guy the credit he deserves. He sure pulled a fast one on ME with this whole transition.... lol.
Good luck & Take care.
JT