Lol, shergill, I feel the same way -- it's at a different angle, I think, because of the bezel change than what I was used to with the original iPad (and the iPhone for that matter).
I completing understand this, the iPad2 taper looks awesome for lowering the visual profile but it ensure the dock, USB plug and most high headphones don't sit right...
If the iPad3 comes out without a taper and with retina I'll guess I'll update because it's driving me nuts.
After using it for half a month, and plugging in about 10 or 11 times, it gets better. It's no longer as difficult, so just keep using it and it will start to "break in"