(1) Game one the gameplan might be very linear. After boarding everything gets much more non linear. It also depends on the Version you are playing.
(2) Can't tell you all matchups but a bad matchup e.g. is E-Tron since Chalice for 0 can be hard to beat when they follow up with a TKS or t3 Tron. Fair Creature decks (except for humans or spirits) seem to be good matchups. I also like playing against fair midrange decks as Jund.
With cards like waker of waves, striped riverwinder and force of negation, is there any chance we can build a blue living end version, that playes the cascade combo style instead of the as foretold/electrodominance one?
I play 3 dragonskull summits for budget reason and they are totally fine in my opinion. I played the deck for more than 1 year on tournaments and had only 1 time where I had to mulligan because of dragonskull summit being no blackcleave cliffs. They are even better when playing on turn (e.g.) 6 followed up by a reveler...
I have to say that I play Looting and Charm since I don't play the full-cycler-list but a list with streetwrait, riverwinder and a lot of fatties (Iona, It that betrays, etc...)
The thing with blue is that izzet charm is very very good in this deck (or at least it was for me)... You cast your combo, they crack relic in response, you let the relic kill your gy and loot 2 big creatures with izzet charm before living end resolves... the other abilities of this card are also very good and especially very flexible. If there was no izzet charm I would agree on the b/r version.
(2) Can't tell you all matchups but a bad matchup e.g. is E-Tron since Chalice for 0 can be hard to beat when they follow up with a TKS or t3 Tron. Fair Creature decks (except for humans or spirits) seem to be good matchups. I also like playing against fair midrange decks as Jund.
(3) Depends on the Situation
Guess we have a new toy...
This!