Here is a closeup of the section growing upwards, do I want this? Or is that just wasting the plants energy?

That's a healthy pumpkin plant. The flowers will sort themselves out eventually. It's normal for either males (usually) or females to show up without the other gender initially.

The vines will climb things if they are close and no, it's not a problem. No reason at all to chop it down. If a pumpkin does form on the vines that are climbing the fence you will need to make a sling to support the pumpkin to keep it from tearing the vines down. But if you don't want it climbing the fence, you can either snip the tendrils holding it to the fence so that it will lay back on the ground or just train the vine back down. If it were mine I'd leave it alone and let it do what it wants (unless it started growing into the neighbor's yard).

Rodney

O, ok. It's actually about 4-5 plants I think. They were sprouting in clumps in the compost pile (in the background of the photo above), and it was hard to thin them out initally. So I picked out 4-5 clumps and set them about 10-12 inches apart. So there's probably about 4-5 actual plants there. So excited, a few years ago I got a 22 lb pumpkin when the compost had pumpkin babies the first time ;) Hopefully I'll get a few this time around as well. I've never really fertilized, or learned the proper watering technique/amounts, besides watering the ground, and trying to keep the foliage dry. I have a feeling I water too often (once or every other day when it's over 80F).