Chrome has problems processing page-break-after, and page-break-inside this is a known bug and Google has said a few times to avoid using this type of styling since not only Chrome but many more browsers run into problems using it.
You should consider styling the tables thought DIV's rather than the tables themselves. Personally in this day and age its normally best to avoid using tables as they are not as flexible as DIV styling.
DIV styling as mentioned is more flexible and easy to work with and looks almost the same on all browsers since browsers tend to render tables differently across browers.
Here is a simple example of how to style the first table you have in DIV and is by far pixel perfect but should give you an idea. Almost the same with some improvement but without the font you use doesn't look as good, doesnt use image as the background which is ++ :P
CSS
#page {margin:0 auto;width:960px;padding:20px;background:#99deea;}
.myblock {background:#c1ebf2;padding:20px;border-radius:10px;}
.innerblock {width:33.3%;float:left;}
.innerblock h3 {font-size:20px;text-align:center;color:#424242;font-weight:bold;text-shadow:0 0 3px #FFFFFF;}
.innerblock h4 {font-size:14px;padding:10px 0 0 0;color:#778A2C;text-shadow:0 0 3px #FFFFFF;}
.innerblock p {font-size:16px;color:#7A8634;font-weight:bold;padding:0 0px 15px 75px;text-shadow: 0 1px 1px #FFFFFF;}
HTML
<div id="page">
<div class="myblock">
<div class="innerblock">
<h3>Spencer Hill</h3>
<h4>Recent Work:</h4>
<p>Example Work Number 1</p>
<p>Example Work Number 2</p>
<p>Example Work Number 3</p>
</div>
<div class="innerblock">
<h3>Becca Ward $500</h3>
<h4>Recent Work:</h4>
<p>Example Work Number 1</p>
<p>Example Work Number 2</p>
<p>Example Work Number 3</p>
</div>
<div class="innerblock">
<h3>Rachel Tourville $150</h3>
<h4>Recent Work:</h4>
<p>Example Work Number 1</p>
<p>Example Work Number 2</p>
<p>Example Work Number 3</p>
</div>
<div style="clear:both;"></div>
</div>
</div>
I've saved this code online for you to see and test, take a look at http://jsfiddle.net/tsd4V/
Again this is just a better method you can use table styling but don't use page-break if you want good cross browser compatibility.