strat question, 10/20 scenario fixin big leaks yo

[Hobb]

10/20nl, h/j 1800$, button $1300, hero $2000. live.

folds around to Hijack, an ok slag player, a little too predictable, very wide pf range, relatively tight postflop
H/J raises to 80. Button (pf callin station) flats.

You sittin in SB with 63, raise to 300. BB folds, H/J calls, Button calls.

Question 1:
How often (if ever) do you find yourself in this spot (rr w/"trash" out of blinds)? What is wrong about arriving at this spot, and is anything good about it?

Question 2:
If you ever find yourself in this spot, (H/J with 1500 behind, button w/1000 behind, 1k in pot), what's your plan to the flop? is it HIGHLY flop dependent, MEDIUM, LOW?
i.e. maybe you plan to shove no matter what. maybe you plan to c/f to a bad flop. maybe you want to check dark and reassess, etc.

If flop is 654, what?
If flop is 622, what?
If flop is A62, what?
If flop is AKT, what?
If flop is KQ8, what? etc.


obviously feel free to ignore w/ever parts of questions... cause i would appreciate any input at all into this type of simple situation.. i feel like the answer should be simple but i believe I don't play it to maximum +ev

Random Question 3:
Is H/J call more dangerous than Button's (pretend they are unknowns)? What if H/J folds and B calls? Or if H/J calls and B folds?

ty sirs