I know how to do this without Kentico, so your example is appreciated, but doesn't help me resolve this in Kentico.
In my mind, this is 100% a Kentico question to get the mark up where I need it.
I would gladly use repeater, but I don't know how to determine the data in the transformation is at the half way point and it's time to finish off that column and start a new column.
With data: one, two, three
I would need to spit out:
<div class="column">
one
two
</div>
<div class="column">
three
</div>
So it comes down to knowing when the data row index has passed the half way point and outputting additional markup. If I can do that with a transformation, then that solves my problem and the web part doesn't matter.