I can't comment on your image since the image sharing site you're using is currently down.
But as far as criticals go in 5e:
You must roll a nat 20 for a critical. Modifiers boosting a end result to 20 doesn't count, it is specifically you roll a 20.
Certain effects such as class abilities or items can increase the range of a critical roll, for example Champion gets a bonus range of 1 so a 19 or 20 on the D20 will result in a critical.
These effects can stack, so with enough of them you can get to a point where you crit on every roll. Though only Nat 20 benefits from the auto hit, every other roll would still need to have enough modifiers to overcome the target's AC (With Nat 1 being auto fail)
