@Chuckie - sounds like I'll be good w/a little 2-stroke oil in the cylinder.  On my 4-strokes, I recall it was suggested to use a 'capful' (of the oil quart container?) in the cylinder then give it a few kicks or push of the start button.  Carb is totally dry at the moment so conditions should be very similar to yours.

@James - the ring gaps are over the pins and the arrow is pointing to the exhaust port so I should be good there.  I could not for the life of me see any indication on that top ring at all of which end should be 'Up'.  There was no writing, indentation or anything.  I tried getting a good edge on look at it as well to see the angle but it looked almost entirely square to me.  This top end came from a machine that recently had the top re-done with very few hours on it.  You could still see most hone markings on the cylinder wall and the piston look essentially new. 

Worst case scenario, if this one is shot, I'll finally spring for a new oversized piston and have a spare jug bored to match.  THEN I'll get it back together and running!