Adam,
Please don't feel bad because I started there too! And don't be afraid to post picks, even if you've made a mistake, it will go to help others and help us trouble shoot your problem. Also make sure you take a look at the faq section on plow set up. There are some real good advice give there.
Now with that said we need to know what condition you plows' moldboard is in. A rusty plow will not work worth a darn I don't care what tractor it's behind. I learned this the hard way. Polish, polish, polish, if your hand slides easily over the surface your good, if you feel resistance from rust or pits in the metal your going to have problems. The same logic goes for the coulter too, also the outer edge of the coulter needs to be sharp. Not like a knife sharp but not all chewed up from hitting rocks and such. You may even want to remove the coulter, some times it will tend to push the plow up out of the furrow if the ground is dry. Is your ground damp enough to plow? If ground is too dry it won't turn over very well and some times the plow won't even bite in at all.
Oh and the first pass is always going to look a little rough anyways due to the tractor not being tilted over at the correct angle. The second pass is always better looking and usually a little deeper.
Kind of funny too, my Cub originated from Cheribusko, Geiger equipment. I don't think I spelled that right but Whitley county anyways.