Hi Renee,
I think you should bite the bullet and get him pull-ups for daycare because it seems like he's receptive to being trained, at least at shcool, which can be enough to get the ball rolling.
My DS did much better at daycare than at home. He was 2 1/2 when they really started training him- he was one of the youngest in his class, but one of the biggest (75-90% weight and height). He really had no interest in the potty at home at all.But at school, his friends were older and all doing it, so he did too.
That being said, he really lagged behind at home and we kept him in diapers longer at home and in pull-ups longer at home when he had moved on to underwear at school. He likes to be a baby at home but he loves being one of the gang at daycare so it helped a lot- honestly he would not be potty trained if daycare hadn't really taken the lead with him.
We have a similar dilemma with DD. She is in the 2 year old room where they get potty trained but she doens't turn 2 until the end of December. She's interestred in the potty as a physcial objectand likes to sit next to DS when he's using it but at home she has peed on the potty only once a couple months ago. At school she goes to the potty several times a day with her clas and has peed in the potty numerous time.s DH & I are thinking of trying to jump start her training over CHristmas break, but she will literally be just 2 then, but we know that once they go back in January the push will be on a school. But I do worry that she's still a little too young and it wil delay the whole thing.
The way I see it, one of two things will happen
1) they get it super easy and ultimately save us money on diapers and pull-ups or
2)they don't take to it immediately and will be trained when they are 3ish (hopefully not later!) ! :-)
I'm trying to be optimistic ! Good luck!
Vickie