didnt read al the other posts but heres the first thing youll run into.
you rings are old and worn out and your going to get blow-by like no tomorrow, which creates its on set of issues like the PCV valve popping right out of the intake,lol
heck on my highly modified 302 (non-power adder) i have plasma chrome moly rings and i run 12:1 compression and it wasnt uncommon for me to blow my dipstick right out of the oil pan

the way i had to solve it was with an evac pump
a 302 block will take about 550hp (give or take) before turning into 2 4 cyclinder engines
if you end up rebuilding the motor you should try to find a mexican 302 block, you can find them fairly cheap and are quite a bit stronger in the main webbing and bore and also the main caps are beefier so you dont get main chatter