Apple allowed connection via a regular USB docking cable at the request of companies. The reason things are locked down, including why iDevices have never had removable batteries, is that consumers stuff up their devices with dodgy batteries or external devices then blame Apple when they fail or don't work. Apple certification ensures that peripheral makers aren't making rubbish that crashes your iPhone or iPad.
Getting Apple certification is a huge PITA and is of arguable benefit to something like the Hugo.
Hmmm, maybe I'm a touch more cynical than you Amos, but I've always considered Apples decision to lock everything down and keep all connections proprietary, to be a mostly financial one. It keeps customers in the Apple ecosystem and guarantees the sale of far more accessories.
I don't have a Hugo yet, but the level of excitement and pure audio pleasure being expressed on this thread is mesmerising. This device is quickly moving up my list of essential head gear to buy.
Damn all your ears!