I'd like to start planning out projects that my son and I can work on together. My goal is to create learning opportunities through interactive play, within 20-60 minute time periods.
I'm pretty open-ended on the types of learning opportunities these play sessions may provide. These sessions could cover everything from art to basic language skills to physical coordination and dexterity.
My son is 33 months old. I'd like to get these projects started as a regular activity, and keep them going at least until he starts school. My hope is to transition this into ability-appropriate supplemental education that we can build on top of his future public-school education (my version of homeschooling). This means that the topics will eventually transition to more academic topics (math, science, history, etc.), but for now I'd like to focus on skills appropriate to a toddler or pre-schooler.
To help me develop a list of suitable project, I plan on identifying developmentally-appropriate skills or concepts that my son could work on, and then try to develop fun activities that would focus on those skills.
The tricky part is to identify what skills he hasn't perfected, but which he has the developmental potential to perfect (or at least improve). I don't want to work on connect-the-dots, for example, until he has sufficient mastery of hand-eye coordination to successfully draw from point A to point B.
While there are plenty of documented guidelines for expected milestones, these are typically framed as "by this age, they should be able to do x, y, and z, and may be able to do a, b, and c." The actual age at which children hit these milestones varies quite widely from individual to individual, and any given child can hit some milestones early, and others late.
How do I track my son's progress in a way that will let me keep pace right on the edge, so to speak, of where his ability starts to fall behind his current potential?