Vig is right, you're in for some tough times. I'm just starting to learn rigging myself. I came across this tutorial which may work for you. It's a maya tutorial, but same shit different name (imo). http://www.wonderhowto.com/how-to/video/how-to-create-a-working-piston-using-maya-970/view/
Wow guys, great responses and fast! Piflik, could you please post a screen shot of that file. I only have 3ds max 7 and I could not open it. Also, thanks for that track tutorial link Vig. This is machine is for my own self satisfaction and I wanted to expand my knowledge of just modeling in 3ds max.
Arrg precise mechanical real world machines... How about using an IK chain? The base of the chain starts at #2, and the tip follows the tip of the piston. It would probably be pretty easy to push that past its limits and break the effect, but its probably a good place to start. You can probably experiment with a limit…