Fix my headache, I'm sure it's simple. $30

I have a custom Drupal theme http://stridewellbeing.com/stride

I want some pages to have a two column layout that behaves like this:

When content in column one reaches 500px height the text overflows into column two.
When column two reaches 500px BOTH columns increase in height to fit the content as it's needed.

I would like there to be a checkbox that turns two columns on or off and I would like it to be able to work with existing content without having to copy/paste.

I've posted this question in the support forum, but if someone can set it up in the next few hours for $30 I'll be just as happy.

I already have panels & ctools installed. I'll give you FTP access and you make it happen.

Deal? Anyone?

Jared