It seems to me that any 'dock connector' should be eradicated from a device like this - it's clearly not needed and just messes up the lines of the device.
You should be able to put it on a dock/stand/table in any orientation and have it:
1: charge the battery inductively. I know, not 100% efficient, but when's that stopped anyone?
2: communicate (music/data/etc) over a very short range (2cm?), low power RF link.
If that's not acceptable, modify the 'magsafe' connector to include a data pair and use that - it's contact technology, but would be better than a conventional plug/socket arrangement.
The tech is there and perfectly achievable. Just waiting for a mass market company to implement it. I'm surprised apple haven't done so already!