C.M.
We moved my 19 month old daughter to a toddler bed after she started crawling out and it went great. She slept with her door shut until 29 months so we didn't have to worry about her getting up and roaming the house.
I think it sounds like it's a good time to switch, but I suggest skipping the toddler bed and going right to a bigger one. That way he doesn't have to switch beds in another few years and the bed he moves to can be his bed for a long time. Plus you and dad can snuggle with him, read, lay with him when he's sick, etc. This may help with the transition to a bigger bed and also with him fighting you at night.
Good luck!