Not Ranked
A few opinions - like you need more.
Having read all you said about your two main advice givers, I'd lean towards the old guy. I think he nailed it when he said your local engine guy is a chevy guy, I wouldn't use a quadrajet or an edelbrock.
I'd be looking for a new machine shop if it was me. One that is more interested in doing what you tell them to do and doing it right.
I wouldn't get all hung up on compression ratio. (given the same cam) a half a point only drops your hp by 4%. Start at 10:1 and go big on the cam. Headers will make much more difference than that little 1 point of compression (to power) but it will certainly help you prevent detonantion. That gives you the flexibility to curve your distributor and run more advance.
Desktop dyno is pretty much useless unless you have flow numbers for your heads. I'm also pretty unimpressed by the infulence of choices of intakes. But other than that it's a tool, much better than nothing but not near perfect.
In the end listen to people a little, do a little research and give something a try.
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