Our daughter started potty training right before she was 2, and took to it pretty easily. I know boys tend to be more of a challenge, but we're just not sure what to do at this point.
Our son started potty training around 2 y 2 months, and it started off going well. He was bottomless at home and mostly doing well. Unfortunately because he's also in preschool/daycare, he was coming home with 1-3 soiled sets of clothes a day. As 2 months wore on, he kept having more and more accidents. If he's wearing anything down there, he would just say "it's a diaper enough" and wasn't even telling us.
So, we're in a reset. He's back in diapers, and for the first few days he would still tell us when he needs to go, but now he's stopped doing that. At this point I'm worried that this reset has caused him to care even less when we start back up (in about 2 weeks).
We just kept the diaper on, but used the pull up kind. Took her frequently for a month or two and she just got it. Super easy. However, every kid is different. She was a nightmare to get her sleeping consistently in her own bed and staying asleep. She's 11 now and sleeping is still kind of an issue sometimes.
We didn't do potty training. We simply placed it in a convenient place, showed our daughter what it is, read her a book where some animal toddlers learned how to use it and one day she simply approached it on her own and used as intended.
From there the rest was also a natural progress - at some point she simply said she preferred wearing panties instead of diapers, first at home, then outside.
Everything began when she was close to 2y 2m too and a big breakthrough was some two months later.
One observation: our little one soiled her panties today, during a play outside, because she was simply so absorbed with what was happening around, that she forgot about her needs.
My son simply refused to go #2 in the toilet for 4 years. #1 was never a problem. His mom and I tried everytig we could think of, positive and negative reinforcement. Now at 4 1/2 he is finally telling us when he is ready to go and using the toilet properly. He was extremely stubborn about it until he just wasn't anymore. Lego Minecraft sets were used as positive reinforcement after say,10 consistent poops in the toilet. I do not envy your struggle, but it will eventually pass. I do not know why boys are so stubborn.
It's not gender related. Son was easy, daughter just couldn't feel, when she needed to go until she was a bit over 4 years old. He will do it when he's ready. I feel you.
Not a dad, but I'm a parent and had my own daycare for a decade. If you want to keep up with the training, accidents are likely to happen, although you could try having your kiddo sit and try to go every hour, to try and avoid accidents. Is this feasible for the school to do too? I'd keep the training at home and school as similar as possible, so wear bottoms at home as they're required at school. Just my two cents though. Best of luck!
We used the book "Oh Crap, Potty Training" for our son and he was trained at 2.5 years old in 72 hours....seriously. That book is amazing and I offered it to others with similar results. It's not as hard as one may think.