To Stroker a 360 or Not

I say go with the "strokered 360".
Sounds like bad ***.
Tell your oil changer guy to shut up and go stand in the corner.

Torque is how quick you get to that "same speed"...and that's what counts here when "strokereding" a small block. You can even build the stroker towards running LESS gear while still making a ton more torque.
Regardless...if you build for what you have...the idea everything has to be adjusted or changed is about as solid as a fart.