As far as figuring out what broke the breadcrumb trail, you can always undo what you did to modify the shopping cart until it resumes working again, and then you can try to figure out how to accomplish the remainder of the changes while preserving the working trail. (You are using some form of version control, right? ;-) )
Now to the rest of your question... there is a question there, isn't there? It sounds like you have clearly mapped out the steps you need to take, so converting that to code should be straightforward, with your algorithm in hand...
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