Smashing Pumpkins HOWTO
No, not the altrock band, but the actual act of forcefully destroying large winter squash! To maximize pumpkin-collection and pumpkin-smashing, you should have friends, a car, flashlights, black clothing, and a good idea of the layout of the area (access and escape routes).
The Clothing
Wearing black is a no-brainer. Hot pink and white jumpsuits are inappropriate for stealing anything, let alone pumpkins. (However, if there is to be a decoy in your group…) Black jogging pants and hoodies can be had for $8-$15 a piece depending on where they were purchased. I would recommend plain jogging pants over the swishies-- and generics over the name brands. For one, you don't want to make more noise than you have to if you are going to grab pumpkins from a lit-up front porch. Second, you're likely to run, fall, drip pumpkin guts, and get dirty in general so why pay the extra $$$ on name-brand shit that is no better than the cheaper generics. Your call.
One minor point to think of is, should you end up in civilization, you may want to look normal. So wear or carry clean, less criminal-looking clothes. A Denny's breather or a run-in with a police officer may be times your clothes can give your activities away.
The Car
If your aim is to collect over a dozen beautiful orange orbs and you drive a Geo Metro, forget it. Get someone with a real car. A truck with a cab, an Eagle, a hatchback.
If you're going to be pulling from the same neighborhood, you'll want a quiet car. Shitty loud cars that wake people up from deep sleeps are OK if you're going to stop once and go on to another area, but why add the pressure? I prefer collecting pumpkins as care-free as possible. Which leads to my next point, the simple pumpkin-aquirement algorithm.
Have your driver drop you off at a certain point and then drive ahead to the next stop sign and wait to pick you up. In a given suburban block, there'll be just about a carryable limit of pumpkins (with a bookbag). You can avoid backtracking (innefficient and dangerous) in this manner. Not rocket science, but something to keep in mind. If you live in the country, you don't have to worry about this, as houses are farther off the road. Generally the suburbs are the best place to get pumpkins, so if you live in the city or country, go to the 'burbs.
The Tools
Flashlights flashlights flashlights. If you do your collecting pre-Halloween, and late at night, there's a good chance things won't be lit up. Thoug letting your eyes adjust to darkness and then working in it is best, there may be times you'll want a light. What's that slime on the pumpkin? Ewww, a big fat fucking SLUG! Gross. Of course arranging pumpkins in the back of the truck or car is aided by light.
Bookbags can aid you on carrying extra pumpkins and also act as a place to store flashlights and extra clothes. Common sense. But since you're reading this you and are considering doing this you probably have none. Anyway, again, black is better than jungle leopard pink and green print Barbie backpacks, but if that's your thing just be prepared to get nicknamed "Gay Fag the Pumpkin Snatch" by your jailmates (yes, police DO arrest and detain pumpkin-snatchers, usually as trespassers, minor thieves, vandals, etc.).
Goat-skin gloves not protect your hands from abrasions caused by pumpkin-shaft spines but also feel soft and retain heat well. Spend the extra $10 and your hands will thank you.