I like the A-pillar if you can make it flush. If it bulges out - from anywhere for that matter - it won't look integrated, it'll look molded on.
With that in mind, I'd make your housing flush, even if the I-pod protrudes out a bit... even if you only do a half-depth housing or something, you can make it fit tight.
I can get virgin tightness with proper technique and a router table with a flush trim bit... to the degree that if you want a pressure fit in an upholstered panel, you have to use the vinyl in the jig to account for it.
With that in mind, those techniques work much better, much more accurate, and a much more finished, custom looking panel (you know - the kind that are so custom you'd swear it came from the factory?

) for what you are looking to do.
These guys will do wonders for any fabricator, anyone who hasn't already:
Top bearing flush trim bit and oversize bearing kit
It's really the oversize bearing inserts that let you do the flush-trim that will inherently end up oversized by some proportion, that let you reduce it back down to an exact cutout replica.
Put down the fiberglass - the absolute best fabriction tool is a smooth top router table, flush trim bits and bearing kits. No joke or exaggeration - and perfect for this for sure!
Check them out at either Select Products, or we actually have this guy come to our shop a few times a year to do training, and he's constantly stocking the best of the best for fabricators:
http://www.mobilesolutions-usa.com
You'll be able to build that thing so tight you can pressure-mount it even if you opt for your ceiling and live on a dirt road.
