Anything else going on with him? My boys went thru quite a few phases that messed with their sleep....teething, milestones, post-illness/travel...
I usually went with what they needed as long as they really seemed to be needing it and it wasn't causing a big issue for me, and when it seemed to move more into the habit realm then we'd go back to old ways--sometimes that meant dad soothing at times when I normally would have, or letting him cry for a few minutes at a time (I am so not a fan of cry it out methods, but my younger son really gave us no choice) as long as he didn't sound hysterical.
We're in a new phase ourselves...25 month old son always nursed and then leaned for the crib, I'd ask him to cuddle first but he'd say no. Now he tells me to walk him around and sing, and no amount of it is enough! So i've been cutting back how many songs I sing and warning him "time to lay down after this song." Sometimes I have to sit by the crib for a few minutes until he chills out.
Maybe sit or lay down in the room for a few nights, if that works then you can work your way out of the room. Or a night light can help (or getting rid of it).
For my guys, there was usually improvement on the 3rd night of trying something new--if it was going to work at all.
That's kind of a hard age, old enough to really complain but not old enough to really reason with!
***edited to add: it also depends how you feel about having him in your bed. I, personally, am a big fan of co-sleeping. It's not a right or wrong thing, just how it works for you. My first liked it, my 2nd didn't--that's the only reason he's been in a crib.
Good luck