I like the idea of what you have done here. The only thing that scares me about adding this functionality is that is seems very complicated for a basic user to accomplish. Because of this I believe we need to keep the GearSwap plugin that can work with almost 0 interaction. I think a better solution would be to make gearSwapExtreme a seperate plugin that requires GearSwap to function. That way if I add statuses and other gear and features you do not have to recompile your entire code to keep with the updates. Right now your version doesn't include the latest bug fix or Harrington Waistguard for example.
The Bug Fix may fix the issue you speak of in regards to not equipping your original gear as that is exactly what I aimed to accomplish.
Lets talk about it on IRC next time you can. I noticed you sent me messages but were gone before I got home to reply.
Oh yea i just remembered, GearSwap Extreme can work with or without user intervention, if you don't do anything it'll just use your default statuses and default gears. That's why i propose to include it into your project