Sometimes he resists because he is frustrated. He may truly want some goal, but he encounters difficulty and wants to give up. So sometimes I push him to keep trying, to persevere.
I call that the 'balanced-push' and conceive of having one hand on the child's back and one hand in front on the sternum so that when I push from behind, I don't topple him! I pretty much am willing to try this with anyone who looks to me like they could use that sort of hand. I think that if you are astute enough to be able to read a child this well, then you are paying enough attention to try the balanced-push and see what happens.
Humans, including children, are very complicated creatures, and it's more about close observation and trial and error than having a set of answers that work for everyone in all situations.
Of course - knowing oneself and dismantling the hot buttons helps too.
When my son was 3 I was doing a lot more balanced pushing around building character and gross motor than around academics. With the academics I was trying not to coleslaw him, so those topics I used the idea that if he was having fun, and I was having fun, then it was probably ok. When it came to fine motor development I took more of an 'attractive nuisance' approach - I did try to leave things around that would help him develop the fine motor skills even though the perfectionism was slowing him down quite a bit in that area.
In general, I think we should reclaim 'hothousing' as a pride word. As a group we truely enjoy so many activities that other would perceive as 'torturing the kid' that I'm ready to say - Yup, I'm a hothousing helicopter mom - and if you can think of any other labels designed to intimidate parents I can be those too!
If you are trying to find fun handwriting readiness stuff, have you looked at
http://shopping.hwtears.com/category/GSSI'm looking forward to hearing about if they seem useful to baby gifties, as I didn't find out about this website until my son was elementary school aged.
Smiles,
Grinity