HELP! Should I stroke my '69 351W?

I have a '93 ex-drag GT that was doing 9's and I'm im mid-process of a street legal engine build-up. The car has a 10pt cage, full drag suspension and the previous owner was nice enough to give me a Cartech fuel system(any help on installing it would be helpful)also. I pulled a '69 351W out of a Cougar and it has already been bored .030 over and is in a hot tank currently. My question is whether or not I should stroke it to either 377 or 393? I am VERY worried about it lacking the 4bolt main and since it's going to be driven daily hard, and occassionaly at the strip, I don't want to break things if I can prevent it. My parts include a set of Edlebrock Performer heads and Performer RPM intake, 70mm throttle body, 30lb injectors(are the TB and injectors to small for a stroker??), Cartech complete fuel system, cold air induction kit. A you can see I still have a way to go including a C-4 tranny, mass air meter, CPU chip, etc. but the time has come to make the decision as to whether or not to stroke it. Also, it has to be street legal passing Massachusetts air laws. Any help would be appreciated I'm a rookie that wants to kick some Chevy butt.