I replaced my wordpress theme today. The new one looks very very similar to the old one, I know, but the code behind it is more capable. The new theme handles something wordpress calls 'widgets' to make manipulating the side bar easier. I also think I understand the css a little bit better now, so my edits to the provided style.css were less arbitrary and hackish.
I am not 100% pleased with the result, but I feel that it will be more possible to move forward from here than it previously was.