Enivironment vs. Posed photographs

My son is extremely hard to photograph.  He is very cute and has an adorable smile.  That being said, capturing his essence with the lens is hard.  He is very busy, he doesn't care about the camera, no amount of bribery will work, and it's hard to get the energy/patience to actually want to do a photoshoot with him.

I've tried a few things to make shooting him easier, like jam him in the high chair so that he has a seatbelt so that he's only in one place.  I think I could probably do that with the car seat too.  Problem?  Car seat and high chair aren't very cute.  Even with a background covering up the high chair.

So sometimes, like in my park photoshoot and this current post, I've tried following him around and just photographing him in his natural environment.  Problem?  No smiles, hardly any facing towards the camera (I get about 150 pictures of the back of his head) and at the end I am exhausted.  He's everywhere!  After all, I am a mom and I want the typical "mom" picture - my baby smiling looking so handsome towards the camera and showing himself off to the world in the most flattering picture possible.

This is always my dilemma when it comes to photographing Dean - where am I going to take the photos and what types of photos am I wanting to take.  Your thoughts?  Any ideas of places, locations, tricks to photographing toddlers?

In this shoot, I let Dean run around the backyard and I chased him.  Didn't get any of the typical "christmas card" photos but it was a bit more of an artsy shoot where I just played around with composition because Dean wasn't really posing for me.  What do you think?