If by left content you mean the categories (wines etc.) being only those 4 categories, I'd guess the height won't change.
I tried duplicating the messed up page, but now it displays correctly, I thought I had misplaced the code in the tpl_columnar_display.php so I tried a couple of "misplacing", and it is either ok, or no page display at all, nothing close to the problem I encountered yesterday.
Anyhow I attach the screenshots of different configs I tried so you can perhaps spot the problem, like case 4 where the images in the new products don't always stay in the grid 3x3, when I refresh the page sometimes they do, sometimes they don't.
Without the negative margin the boxes stay down even with the conditional tpl_columnar_dispaly.php file.
case 1 - homepage with the negative margin

case 2 - homepage with negative margin, and max images for the new products set to 6 - the featured overlaps the new box

case 3 - homepage with tpl_columnar_display.php with negative margin

case 4 - homepage with tpl_columnar_display.php and no negative margin
