first seriouse drag motor
 

i have a lot of questions so bare with me.
ok i have an 86 silverado i want to drag(no streat). i have a standard 4bolt main 350 in it now. i want the most possible hp i can get out of it. it will be carberated. and most likely forced induction. i plan on sonnic checking the block. i read that you can fill your jornals before you bore to get more cubes.
-how dose that work with cooling?
-and how many cubes can i get out of bore and stroke and still run a power adder?(with the jornals filled if need be). then what will my over all cid be.
-and last i have 5500 lbs truck, i can strip some weight but its still gonna be heavy, how should i build the motor for the quickest 1/4 time?(build for top end and get my bottom with gears, or build for mid range because of the weight, but what gears should i run?)

i understand a lot of this will depend on my block, so lets assume its a real solid, typlical 350.
i also plan on running a th 400 with a tranny break maybe a 4000-4500stall, but i have'nt purchased a tranny yet so its still up in the air.

ok i know thats a lot but any help would be great.