This year, since he was three and potty-trained, we planned for him to take an actual lesson and start skiing in earnest. However, when we got to Steamboat, we realized they had full-day lessons only for those 3.5 and up. Will was a couple of months shy, and while we might have been able to sneak him in, we felt like it would be better for his first lesson to be only an hour or two. For younger kids, all they offered was an on-snow childcare program, where he'd be there all day but only spend one hour on skis. The cost was $260 for one day (over twice the 3.5-year-old price, where he'd actually spend a decent amount of time on the snow!). This seemed a bit outrageous since we had my parents there to provide childcare.
So we reversed our decision to put him in ski school and once again went after-hours to a little municipal ski hill in Steamboat, where he skied for $5 and our lift tickets were $7.50. After two trips down the bunny hill with the harness, Dad was exhausted, Will was happy and we called it quits. We felt like we'd made the right decision as Will really didn't seem quite ready to bear his weight on the skis. I think next year he will be ready for a serious first lesson. In the meantime, he thinks he skied and it was fun, and fostering his interest in the sport was our main objective.
I have a video of him skiing I may try to post at some point, but in the meantime, here are the pictures we have...
(That tiny little two-person blob you see in the middle of the picture is Andy and Will skiing down the bunny hill at Howelson Hill.)