Neither 1st nor 2nd generations seem very easy. However, the "only" problem I had while opening 1st generations is a little minor bending of the case on a couple when I first tried it, and I broke a headphone jack once (now I'm more careful!) but both of the 2nd generations I managed to shatter the digitizers. One while opening it, and one while closing it. So I'm of the strong opinion that while not easy, 1st generations are easy-ER than 2nd :) I don't ever, ever, ever want to touch another 2nd generation iPod unless it's in perfect condition lol :)
First hold down the home button & sleep button until the apple appears. Let go of the sleep button (but keep the home button pressed down) till the apple disappears. Let go. It should show the connect to itunes screen shortly. Connect to itunes and do a restore. If that doesn't work double check the battery connections and place tape over the soldered portion of the wires, to be sure they aren't coming in contact with the case or each other. If that still doesn't seem to work, perhaps the battery is dead/ almost dead so you may want to leave it to charge for an hour or so before trying to reset it again. Good luck! P.S. These are just some of the fixes that have helped me, I'm sorry I never heard about a boot file on iTunes.