Going back to your original question, As I have a mill, and a little bit of experience, I would deck the blocks (take off .020"), do a multi angle valve job (seat with would depend on if you are driving it on the street of just racing it), CC the heads, then take a small cut on the heads to make sure they were 100% flat (.010" at most). Frankly if I were doing it, I would go to the max overbore with out doing sleeves.
Sean's stroker crank would really make me think. I've done strokers before, and have had good luck, but every stroker I have done required one or the other of a shorter rod, or a special piston. On the motors I have built, strokers seem to give you a boost in torque and and big bore kits seem to boost HP. If I only had to do one, I would go with a stroker for the street and big bore for the strip.
Of course If it were really me, I'd be doing both. One of those things where the amount of money you spend to get there, might as well do it all at once.