If you want to submit Word documents to Smashwords and you don't want your ordered lists to start at 1 ... then I simply don't see any other recourse but to manually number your ToCs.
Even if you could get the epub created with an ol that started at something other than "one", it wouldn't display consistently across the range of devices/apps out there reading it. It's always been an issue that most people have solved by just not using ordered lists at all.
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