what's.this.widget.crap?

I was all excited about changing my blog layout. Like my room (which is painted a neutral color so I can switch the bedding and subsequently the feel of the room), I get tired of having something look the same all the time. I'd checked out different templates before, but apparently not since they set it up to be "easier" for some people. While some of the options for layout are easier, I now can't figure out to customize the content on the sidebar. I figured out enough html to be able to enter images and categories with the old layout, but now there's some weird widget business going on which is giving me a headache. If anyone knows how to help me out (ahem....my favorite 26 yr old brother....ahem) this is what I need to know:

How to stick in a heading like "books I'm reading" followed by a list of both images, and type. I have one that's kind of working, but I can't add another photo without putting in a whole new heading which I don't want to do.
I also want to add a photo and either make that photo a link to another site, or add a link to click on below it. I tried to enter the html that I know (like using a href="..." and /a to enter in a link) but keep getting an error message. Clearly I just don't know enough about widget to figure out what to do. It's unfortunate because they're obviously trying to make it easier for some people. I guess I just like to make things difficult.