Well, it only took 3 months, and I hesitate to mention it for fear of jinxing it, BUT it appears that Asher has finally started to adjust to his new daycare.
Really, who can blame him for having such a hard time? His daycare environment went from a warm loving home, with two adults and 2 other kids (with lots of other family members around on a regular basis), to a room with 2 teachers and 15 or more other kids.
Still, I didn't see it coming. Based on our visit where he played on the playground with the rest of the class while we finished the tour, and he marched in line when they came in, and showed no distress at all, and given his general laid back attitude and abundance of confidence, I just did not anticipate 3 months of sobbing every time we dropped him off. Or every morning him asking us "no go to school today?" and then the dread that would accompany an affirmative response.
Deenesh and I have always really liked his daycare. They do yoga, and learn Spanish and sign language. They have great facilities, and happy, positive, caring teachers. So it's a relief that Asher seems to be starting to agree with us.
We tried a lot of different tactics to help him adjust. We made up a special song about going to school. We would load up his special teddy bear with mommy and daddy kisses so he could get them whenever he wanted throughout the day. We spent time talking about how fun school is, and the fun things you do at school, and the people you get to spend time with. We gave him special school-only snacks for lunchtime (like go-gurt!)
Of course, the goat on the slide probably helped.
And I think the pony ride didn't hurt either.*

And I'm not going to question the fact that the big turning point seemed to happen the week that I was at a conference in San Francisco, because the fact of the matter is, I am just so relieved that for the last 3 weeks, we haven't left a sobbing toddler at daycare, but have left something like this instead.

*No, the school does not normally have goats are ponies in the playground. They had a special fall festival with animals and special crafts in each room, and I will admit that that seemed to be the start of him revising his opinion about school. But the real breakthrough did come when I was in San Francisco.