The siding can't be that far in front of the sheathing, cause the top of each course is nailed into it.
One of the problems people run into is the fact that the vinyl "boards" are beveled, so the numbers don't hang right. There are blocks you can buy (same place as the siding) which are contoured on the back to mate to the "boards;" these are designed for finishing the installation of siding-mounted light fixtures.
And then, since this is all about woodworking, you could always take a length of 8/4 board 5 or 6 inches in width and shape it down to fit the contour of the siding "boards." The backer would be nailed along its top edge, and the numbers nailed or screwed into the backer. A good coat of varnish would be nice.
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