Is it surprising that it doesn't work well? Not really. The compromises are pretty extensive. And between the users demanding thin phones and rugged connectors, its really really hard to do that with anything other than perhaps titanium.
I have a bunch of computers, my oldest was built in 1968 the latest was built last year. Invariably the port complexity goes up with the older computers, and connector reliability also goes up. I've got AUI cables for Ethernet that work as well today as they did in 1984 when they were all the rage. I've got 50 pin SCSI-1 and 36 pin Centronics printer cables that are reliable and functional. I've got computers with 3 of the four USB 2.0 connections on them unusable either due to fusing issues or mechanical strain. I've got a phone handset (my developer's version of a Nexus 1) with a micro USB connection that won't hold the connector in the plug.
I guess the bottom line is that we can make really reliable and ugly connectors.