Not really fair comparing a built and stroked motor to a non stroked. Take the same methods used to build up your SB and apply them to a BB and there isn't a snowballs chance in hell you'd be in the running. For that matter- you have the additional upper hand with your OD trans. You get to have your steep gear, and top end too so even if you were to race a car with similar power, odds are they dont have OD and eventually you will pull away. CHEATER!
But back to the OP topic. Hell yes- do the BB. I loved my 67 Barracuda. I had a mild 440 w/ .509 cam in it and it drove and handled great with upgraded t-bars. The only thing I would do different if I was to do it again would be to add an OD trans like my brother (the CHEATER) so I could drive to farther out shows with the 4.10 gears I had.