Oh, one little warning, when you pull the rod out, oil may shoot out the rod end port.
Well, you already figured out that the orange piece is the wear band. You can see the split, easy off, easy on. Look for something similar on the piston seals. I think I see something like a split that would make for easy removal. I am impressed, that looks like a nice quality cylinder assembly. Large enough wear band, good quality piston seal, heavy piston, extra o-ring on the gland. This is not a cheapo set-up.
Take a flashlight and inspect the cylinder bore very thoroughly. Look for differences in the pattern of the light. Shine it up there and you'll see what I mean. The glare will come off the cylinder wall in a nice pattern, check for anything out of the pattern. Also look for debris, burrs, anything that could have caused fluid to go past the piston seal.
And, remember to put your daughter's pipe wrench back on the Fisher-Price workshop peg board when you are done.