Howdy, I think I understand what your trying to ask. I used to work for a label printing company & had similar issues when swapping over from freehand to Illy. As we stepped up & added bearer bars direct into ai, and concidering ai insanely aligns to the artwork outline not the mask, it was much easier if we could have an exact bleed.
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How do I join the outline of the cutter once I have deleted the internal cuts and folds, without getting the join error?
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You have somewhere in your path mulitple endpoints. Where in Freehand you would have just selected your path & told it to close path in the attributes window, in ai you can either select your path with the direct selection tool (the white pointer) & a blue line will "joint the dots" exept where your path isn't closed. You can then select these two individual points with the direct selection tool & hit command J to join point.
Another way is to select your path & in the pathfinder window hit the "Trim" button. This will join your endpoints but beware, it won't work if you have more than two endpoints in your path.
Play around with this pathfinder window, it was extreamly useful to me while I was working with dielines.
After you have your closed path, you should then be able to proceed to offset your path through the Object menu, then path, then offset path. Where you used negative numbers in freehand, you will have to use positive in ai.
I hope I understood what you were asking! There may be an easier way, especially if you have a complex path to deal with, but I haven't found it yet!
Cheers!