Ya know? I think its really all in your EGO. If its gonna bug ya later, get the big block. I have a 514. It is perfectly driveable........though I admit your a ways out before you really put the foot to the floor......
I can't imagine there is much wrong with a good 351Windsor.
But will you or won't you second guess yourself. If you are committed and happy with a SB, that's a great choice.
I could be wrong, but I think the one overplayed issue you mention is the weight. You can still get to 50/50 with a solid frame and rear end.....and with aluminum heads and manifold I question whether the big block handles much differently.
I think where the handling issue comes in is that you have to feather the pedal more in and out of turns and its harder to gauge and there is more risk of spinout. More often with a SB, you can just floor it and you might be ok, while the guy in the big block is trying to find the traction line..........and may come up short or long................
Then again with the big block, with all that torque....it is probably easier to flip the back end more abruptly if you need to in a given situation..............