Struggling with Pro

Hi everyone. I am trying to do something that is simple In Corel or Adobe but the means in Carbide pro is causing a fair bit of hair pulling. I am trying to do a simple (should be) cutout of Vancouver Island. I am using an outside offset to simplify the coastline for the bottom layer (1/2") then another layer about 1/8" with the fine details carved with a 60 degree V, then a half inch taller than that, the house number that runs all the way to the table. I can get the first 2 layers ok, but when I add the numbers, the tool path buts the numbers and the edge of the island from each other, I need the numbers to stand the full height of the material. What am I missing or doing wrong?
Island Address.c2d (764 KB)

Please post the file in question.

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