like others have stated, depends what you want.
IMO if your going for the 250 head go for a direct mount 2bbl, the HP increase will be felt in the seat of your pants and you'll be grinning ear to ear.
I really enjoy my 264/274 110* CSC, it has a great bottom end torque (150-167 depending what carb and air temp) and usign the 1bbl mounting hole, I have made 127hp with a 2bbl adaptor, now if it was direct mounted I'm sure I would be in the +140hp range. now over stock I was pulling 68hp
the only down side if there is one, is I make the HP late, roughly 100+hp around 3500rpm (ATM with a 1bbl)
the bore, if your not going blown, keep it round and healthy, IIRC the more you bore out the more heat the cyl walls soak and less heat is expelled out the exhaust.
balanceing the engine will produce a smoother running experience and IMO a more even wear and tear.
for street gas a 9.3:1 CR is good, depending on elevation you might be safe running 87 oct.
let us know some more specs, you can tell the forum 'lights' up when someone is about to rebuild thier i6