Unfortunately yes, all the failures I have seen with this (my own '06 and at least 4 or 5 I have done for other people) all started with the female sockets being spread slightly so there wasn't a good firm seating of the male pins.
In some cases the resulting resistive connection created by arcing resulted in the plastic housing being overheated to the point of melting (as per the photo in the document) - something you don't want.
The only reliable way to address this is by cleaning and reforming the female sockets which are on the bike side so won't be helped by a replacement regulator (if one or both sockets are deformed).
The other thing to avoid with a poor physical connection between pin and socket is dielectric grease. This does a great job at keeping moisture out but ONLY if there is good physical connection. It is an insulator or very poor conductor of current at best so will only add to you problem when there is a poor fit with pin and socket.
If you aren't confident tackling this from the old document hit me up with a PM and I can do a step by step with multiple detailed photos for you (I still have the '06 Uly).
Some folk have cut these two plugs out completely and soldered / crimped the wires together directly but I would consider that a last resort and more difficult than cleaning/re-tensioning the original female sockets.
If you know someone with a proper Deutsch crimping tool then the original two pin Metri Pack connectors can be replaced with Deutsch DTP connectors as per the revised Buell VR's but most people won't have that tool ( I do because I do vehicle wiring jobs as a hobby but I'm on the other side of the planet).
