I’d advise against USB extensions as “breakaways” – a lot of the time, it’ll work, but it’s really not meant to be a ruggedized connector for that sort of thing. Every time you trip over the cord and it disconnects, you are risking damaging the connector. The only thing likely to be damaged thing is probably going to be your $2 extension cable… but as an engineer, I’d rather advise you use a connector designed for this type of abuse.
Anyway, I’m not entirely certain as to the point of this, and why a Neutrik wouldn’t work (I’m pretty sure you can install it in the cable compartment, which doesn’t affect the look of it at all, and you’d still be able to store an A-B cable inside the compartment when you travel with it. This also makes it so that you’re only replacing one thing when (not if) the cable fails, because cramming cables into that compartment is horribly abusive to them.
At that point, you could have exactly the lengths you want of USB A-B cables for each location where you play, and you’re not risking signal degradation: USB is only spec’d to perform at 5m, and the built-in cable (IIRC) is 4m… so you’ll be going over-spec with any sort of extension cable longer than 3 feet. This may or may not cause issues (likely to manifest as disconnects). Of course, a standard A-B cable won’t take care of the need for a breakaway, so hopefully someone can provide ideas for that issue.
If you’re dead-set on your “keep the cable in the compartment, add another cable” system, I’d at least recommend using the proper type of disconnect. MadCatz themselves made a 9ft breakaway cable that you can get for pretty cheap, which should work with the built-in one (assuming this is a 360 stick (wait, actually, did they install those on PS3 sticks? I don’t think I’ve ever noticed if those are missing on PS3 TE’s…)). Then you could just remove the short breakaway, and have that connector hang out of your cord compartment. I’m not a huge fan of this solution, to be honest (it will bring you over spec on USB, though probably not to the point that it would cause problems as I’ve run 25’ USB cables without problems; I more dislike it because a Neutrik connector is cleaner and looks better in general), but whatever floats your boat.