Wordpress help: Slider with randomized images from a single category

Hey guys, haven’t posted here in awhile!

Here is my site. After a lot of criticism from this site, I was eventually able to get it to its present state, but there’s one more big thing I want to implement.

The portfolio box on the front page currently shows a static image, linking to a static post. This is because I could never figure out how to do a slider like I want. In fact, there are a few things I want to do involving sliders that I’ve never been able to figure out.

I have a portfolio category, and each portfolio entry is a post. Each one of these posts consists of a title, a description, a custom field for the client, a single image, and that’s it.

I want each post to be able to have multiple images in a slider, but with one image being treated as the “main” image. The others would show alternative angles or snapshots from the design process, something like that.

In addition to this, I want the box on the front page to have another slider that takes the “main” images from the portfolio posts and displays them in a random order, while linking to the post in question (which should open in a fancybox window)

Any ideas?

EDIT: Also, I’m willing to toss someone a few bucks to do this for me, because I really don’t want to be bothered with it. I can do HTML and CSS just fine, but when it comes to Wordpress I basically just paste things together and hope they work.

Basically my ideal situation is that each image in a portfolio post would be a custom field, or something like that. That’s the only way I can really see this working.

Excuse the double post, but I found another problem.

Apparently, when I have my custom theme enabled, the “upload files” dialog on the new post page will not open. If I switch to TwentyEleven it works just fine.

How is that even possible?