Just had time to look at 1 & 2 quickly.

1.) I would tighten up slightly in each pos & 4bet the top 1/3-1/2 of my opening range in each pos & throw in an occassional 4bet bluff.
& see how he responds to that.
a) If he calls I c-bet most flops & get it in very light
b) If he shoves most hands I call with Ax, K10+, 77+

(I might also rebuy to a 60bb stack if I lose the first all in, so there are much fewer decisions to make, just playing my tight preflop range vs his
wider one basically. )

2.) I stop c-betting.
With draws I check call his min type bets
With hands I think are best I bet call min raise on flop & check raise turn