Engine builders

I kindof agree with you, that this guy might be in over his head.I mean who bores a block without pistons in hand? On the other hand if you asked/told him to bore it .020, well then, the shoe's kindof on the other foot.
I know almost nothing about 440s, but if I was to build one, I sure wouldn't "settle for 9.0"
For your stated goal; " It`s just going to be a street cruiser, I want to run hydraulic cam. I`m open to suggestion on what to choose for my goals", I would be moving up for sure.
Just be sure to engineer the whole pkg; Static cr, Dynamic cr, and quench(more properly; squish)