Hey meatspin (nice name bwahaha)
About your third question - I have a kind of big foreskin and masturbate with my hand over the glans and the top of the shaft like you, and I don't have any baseball bat effect at all, in fact my shaft thins towards the glans. So that would imply that you can just enjoy masturbating any way you want and not worry about it
But still I would keep an eye on it just to make sure.
GC