What do you consider a plank of wood? If you are talking about a 2" X 4" or some other small piece of wood don't do it. Hercules and Big max are large pumpkins and as they grow over the edge of the wood they will deform. What I mean is you will end up with a pumpkin with a board shaped indentation on the bottom. It is also very likely that the pumpkin will split at the point where it "falls" over the edge of the board. You shouldn't put the pumpkin on anything smaller than what you expect the full size of the pumpkin to be. You can put something under the pumpkin like maybe a 4' X 4' piece of a tarp.

Plastic won't let water in ... or out. I suspect if you put a bag around the pumpkin it will keep it very warm and humid within the bag and actually encourage molds. If you want to wrap the pumpkin you could try something that is breathable like the floating row cover material. Just be sure you don't constrict the pumpkin as it grows.

I can't tell you if sunlight is what causes pumpkins to turn orange. I can tell you that sunlight does hasten the ripening process. Pumpkins in full sun ripen faster than those shaded by lots of leaves (or anything else).

The yellow stiped beetle is a cucumber beetle - nasty nasty! Thy can decimate a cucumber vine very quickly so you should get rid of them.

Thanks for all the good info. The cucumber beetles, if thats what they are, just hang out inside the open flowers with assorted bees and then when I water the area they fly away. We don't have cucumbers growing. Do they attack pumpkins too?

I read an article a while back (youcould prob. google it) about how in japan/china cant remember vendors were puttling watermelon fruit while still on the plant into boxes to grow and mature in square shaped watermelon.......it is an interesting theory I would try it with one or two and leave the rest alone..that way if it doesn'tg work out you have a couple pumpkins that weren't manipulated...