i am going through this!! it all depends on your level of comfort with buying the pullups, i think lol. for us i am SO ready to quit having to buy them, times are tough and every little bit helps. my son turned 3 in december and has been potty trained since august, however he has only had a dry night here and there, nothing steady, until this week, when he's had 4 dry nights in a row, and has gotten up to potty once a night each of those nights. i feel like he is ready, with a little encouragement. (and i TOTALLY feel like your son is ready!) if he has only had a couple accidents in three months i think he's beyond ready. accidents do happen, in bed just like anywhere else. we did undies for the first time last night, and i am SO excited to report (altho i did get him up an extra time around 4 am to potty, knowing we weren't getting up early being saturday) that he woke up bone dry! and he was SO proud of himself. we've been talking about it for several days and the gratification on his face when he realized he did it was amazing. i would TOTALLY try it with your son. explain to him what's going on, how he's such a big boy now that he doesn't need a pullup, and make sure he knows that he can, and is able to, get to the potty in the middle of the night if need be (invest in some nightlights, i did and my son loves them). let him know he can come get you if he needs help. i think it's time to let him spread his wings mama, sounds like he's ready! if you're worried about the pj's switch to sweat pants at night for awhile. good luck!