Sad to say, but we haven't carved a pumpkin in years. But the last time we did, we worked with someone who had all the right tools: sharp, comfortable knives, fine tools with various sized edges for scooping and detailing, and even some books with design ideas and stencils.
As for designs, we've grown to prefer the pretty ones (left, concentric circles, over the scary ones (below, Loki)...
...but still have a love for everything in between (and never attempted such realism a la Napoleon Dynamite below).
What's your best-ever jack-o-lantern design?
Related Links: Pumpkin Carving Kits
How To: Make Glittered Pumpkins
Look! Pumpkin Carving Gadgets