How much, if any metal shaving should I see out of the filter after initial startup? The oil in the pan was clear but I poured out the filter and it was streaked with gray. Normal? Bad? Very Bad?

Your very first drain will yield some metal this is normal. Just make sure that there are no shavings or larger pieces, the normal metal will be fine and make the oil look metallic.. This should be totally gone by the third oil change.

Thanks, yes the oil in the filter looked kind of like silver metallic paint but no chunks or splinter sized pieces. I rubbed some in my palm and couldn't really feel the grit so it must have been very fine.
I am running a dirt street stock car and all this is new to me. This board has been very helpful. Dare I say my car is a Monte Carlo? I've been to other boards and you guys all seem to know the small block chevy better than some of the other boards out there.