I would worry more about getting the quench right, then the milling(that's just me)

.009 in the hole, and .044 is .053.

If you use a .030" cometic head gasket, then you'll have .039" pretty good.

Right there your up to about 10.1:1

If you go crazy with head milling you also get issues with pushrods etc. Maybe cut .015 off and stick with that

The cometics cost a little bit more, but are reusable, so if you have the heads off once, you got your money back.