You can have overlap in the same menu, eg. you can't have 1 and 1XX, that will always just match 1.
To do something like that you would need to have just 1 which links to another menu action that has $. Link $ to a transfer to 1$KEY and the timeout on no dialing to what ever 1 should go to.
Best way to learn/test this is to add extra Generic actions at point in the callflow that use things like $KEY as an entry prompt so that you can hear what ever value the system thinks has been selected by the user. Once it all works removes these extra actions.
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