Reddit reviews Adorable Toddler Potty Training Pants for Baby Boys and Girls,Size for 9 Months to 3 Years,Pure Cotton,4 Pack (18-24Months, A)
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Four Layers:soft, breathable cotton with layered mesh added in the middle of these cloth pull upsAdorable and slightly water absorbent, more effective to prevent wetting outside trousers.don't soak through immediately like other brand training pants do.Bridge Between Pull-ups and Underwear for Toddlers and Babies, allow baby to still be wet and realize that she had an accident.The elastics are not too loose but not too tight, easy for baby to pull up and down on her own.Washable and softer than paper diapers, prevent baby diaper rash.
I don't have advice on the training aspect. I suspect he will regress a little when starting a new day care. Sometimes, though, watching the other kids help. At that age, other kids teasing won't be an issue.
As far as limiting the mess, my son wears padded underwear with wool shorts when going out. This contains a surprising amount of pee. These cheap kinds worked well for us (but our kid is a different size and shape) https://www.amazon.com/gp/product/B01MSFGX8S/ref=oh_aui_detailpage_o09_s01?ie=UTF8&psc=1 and https://www.amazon.com/gp/product/B07FGDSSH5/ref=oh_aui_detailpage_o02_s00?ie=UTF8&psc=1
Putting wool pants or shorts (sometimes we use the shorts under other pants) really contains the mess. Look into cloth diapering guidelines for washing and lanolizing (making water resistant.) These are expensive but you only need 2; you can get cheaper ones on Etsy re-purposed from sweaters. This is one we have https://www.greenmountaindiapers.com/collections/wool-diaper-covers/products/babee-greens-wool-shorties which is super comfy, but not good for dirt. You can get all sorts of colors and designs; if you are interested I can give you some specific brands to start. I swear when they get pee on them you only need to wash them occasionally (like once a month, but it really probably be hand wash). No it does not smell or feel gross. Look it up; it's crazy.
So if I were in your situation, I'd buy a ton of padded underwear, so he could still feel the leaks and be in underwear. Then I'd buy one pair of wool shorts and one pair of wool pants to wear over that. (And then up it to two for washing later. They'd probably dry overnight, but not every day.)