Z-index only works with absolute or relative positioned elements, using it on anything else has no effect.
Your overlapping column problem is coming from the doubled-float margin bug, which is triggered when you float a div then give that div margin that goes in the same direction as the float - ie; float: left with a left margin and vice versa for the right.
The fix for that is to add display:inline to the #sidebar divs, however you should do that with a separate ie-only css file that contains ONLY the 'fixes' you need for IE to obey, then you call that ie-only file with conditional comments.
Once you fix the #sidebar problem, your #maincontent column will drop. This is due to the padding you have on the left and right sides of #maincontent - remove the padding and the column will pullup where you want it and the images and descriptions will fall into place as you intended.
You can read all about the nasty IE bugs and how to fix them at www.positioniseverything.net.
I would make a couple of other suggestions.
Don't use code like this : <div align="center"> - that kind of styling belongs in your css. See the stickies for help on how to center a web site.
Rather than using the <p class="maintext"> for every paragraph of text inside #maincontent, define the styles for the text like this:
#maincontent p{ properties here} - that way you won't have to add that class to every paragraph  .
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