We're in the process of potty training our daughter who will be 22 months this week. I say process, even though she's pretty much there after 2.5 weeks, but I don't want to jinx it ;)
I looked all over the internet for potty training info and tips, and then I stumbled upon Oh Crap. Potty Training. Now I'm a total convert. Have a look at it and see if it might work for you.
We pretty much followed Jamie's method to a 'T' (with the exception that we had the potty out for months before we began potty training). Our approach was much like yours, and we hoped that one day it would just click for our DD, and she'd start to go pee and poo in the potty all on her own. That was a little too hopeful, now having been through the process. We had lots of pees on the potty - some accidental and some DD initiated - and a few poops.
I was freaked out by the time investment of potty training being that it's the middle of winter and I would be cooped up with my daughter in the house if things didn't go quickly. Because of all our earlier potty work, our DD knew that she was to pee on the potty and knew how go pee when she sat on the potty. Our big area of learning was to recognize when she had to go pee or poop so we could make it to the potty in time.
Jamie's got a lot of tips, and loose approach (and I don't want to spell it out here cause the ebook is $15 and this must be how she makes her livelihood), but our kids sound so much alike. Ditch the underwear and go commando cause underwear does feel too much like diapers. For the first few days you'll be catching your kid mid-pee/poop and getting them to the potty, or letting them know it's time to go, so you pretty much scoop them up and put them on the potty. There's a delicate balance with overcueing, and it's important to let the kid fail a few times, so they know what it feels like to have an accident and they can make the correlation.
The first poop accident was a total surprise for my DD. The next one she wasn't done going yet, and let me know mid-way to the bathroom to empty the potty with the partial poop, and we didn't make it on time. The third poop accident happened at daycare and she let them know she had to go but they didn't make it on time. And I'm not quite sure what happened with the fourth time at daycare. But a total of four poop accidents for a kid who poops two times a day in 2.5 weeks is pretty darn good! We've had many more pee accidents, and equally as many accident free days.
For the first few weeks Jamie says you do a lot of cueing -- and you do! Pottying is really all about you. You recognize the signs and get your kid to the potty on time. Then around week three, on average,she says that most start to let you know they have to go. Our DD started self initiating around 2 weeks and now she just goes when she has to. Sometimes she yells out "poop" (cause pee and poop are both "poop!") or she just goes to her potty. If your DS doesn't know how to work his pants, then I'd start teaching him how to push it down. That's been key for us.
Having had a successful potty training experience (hey, my kid STILL doesn't sleep through the night), I think that what you're calling the "gentle" approach isn't really effective. We're changing the rules on our kids, and they don't really understand, and we're not setting them up for success. Commit to ditching the diapers and go feet first into potty training. I think your DS may surprise you.
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