iPhone 4 Dock Connector Issue

[BulkHedd]

I have an 32GB iPhone 4 that I got in July 2010. I have been using a SendStation PocketDock in my car (charges the phone and gives me line out through the dock connector into my stereo's aux. in.) I've been been very happy with it.
Anyway I recently installed an Otterbox Reflex case on my iPhone. The PocketDock did not fit properly in the opening on the Otterbox. It ended up going in at a slight angle so I used a Dremel tool and shaved a bit off the Otterbox and some off the plastic on the PocketDock and that seemed to do the trick.
However, lately I have been having an issue with the sound crackling and cutting out. I'm worried that my iPhone's dock connector might be screwed, or maybe it's just because the PocketDock isn't sitting flush against the bottom of the iPhone and it's got too much wiggle in it.

Any thoughts?

 

[BulkHedd]

After a bit more investigation I discovered that the metal dock plug part on the SendStation PocketDock wiggles quite a bit so it appears that I should not have shaved off so much of the plastic housing. I'm betting that's the problem.