To answer your first question, yes there is some machine work involved. You will have to take apart the top end & take the cylinder to a machine shop & have it bored out. Most places around where I live charge 50-65 bucks to do that. Everything else is "drop in", but it'll take a while to do the work. I don't know all of the details, since I haven't done this to my quad yet, but you have to remove the plastic, gas tank, carb etc. to get to the top end. Then you have to take the head off, & I think to do that you will have to also loosen or remove the valves, cam, cam chain, etc. Then you can pull off the cylinder & get it bored (have the 416 piston with you at the machine shop so they can match the bore to it). Then you have to reassemble everything, tune the quad (rejet, etc.) & you're set. This kinda sounds like a nightmare to do, but I don't think it's that difficult. Whoever you buy the parts from should be able to help, and you can always post questions here, because there are many who have done it, or are doing it right now. Another thing you can do is take lots of pictures as you tear it apart, that way you can see how it should go back together, and a shop manual will help, too. I hope this long winded reply is of use to you. I ordered the piston & cam earlier this week, so I will probably be doing all of this next week, so if you want more detail, just PM me.
03 Predator w/ TrailTech X-bars & clamp, WB slip-on, custom K&N intake, Edelbrock carb
06 Raptor, Houser +2 A-arms, LSR +4 axle, FMF PowerBomb Header w/ Two Bros slip on, ProDesign K&N intake kit, TrailTech X-bars, clamp & Vapor computer, PC III USB