If you have to cut the siding out its easy enough to slide some j-channel in to give it a finished look. siding is plyable enough and there is a simple tool for spliting the individual siding pieces so you can nail the j and pop everything back together.
If you lag right through the siding will be distorted and might pop in the freeze thaw. I would make a couple of standoffs out of smaller 2x4, then lag through. less intrusive and should still be solid.
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