So....I'm taking my oldest son hunting.  He's only been out a couple of times with me hunting for deer and I think he got bored waiting.

I'm thinking of skipping the deer for now and focusing on something that is prevalent and presents a challenge.

The thought is :  Squirrel

I can't say I have ever hunted the things.

I will be using 22's -- I don't have any .410's

Any pointers or recommendations (aside from skipping the squirrel and hunting the deer).

duck. I love duck hunting more than anything. I still deer hunt but it's not nearly as satisfying

If waiting is a prob then i'd use a dog.

Squirrel hunting isn't hard if you wait.  Go in, sit by a tree quietly, and wait.  Then shoot them.  
Don't move.  
Wait some more. then shoot the new comers.
If you have a chirp call it might help.

If you guys are moving then look for the nests and split up.  Those little raskels tend to stay on the OTHER side of the tree. If you go one way and make noise the rodent will look at you. And try to avoid you by going to the other side of the tree.
Meanwhile he is over there with the rifle ready to shoot.

Works every time.

I started hunting squirrels when I was eight. I started going with my dad when I was six. Same as my dad did with his father. And his father did with his grandfather...

I'd recommend a 20 gauge. Even a youth 12 gauge with light loads.

I highly recommend starting with squirrels. It teaches patience, observation skills, and if you are lucky, multiple and challenging shots. I've got some great memories squirrel hunting with my dad.

Downside: we always had to eat what we shot. And squirrel and dumplings are just ok.

Graduate up to ducks and geese. Shooting on the wing can be frustrating.