He's known to bet in position alot of the times, I've been playing tight but re-raised him preflop on a couple of occasions.

PokerStars No-Limit Hold'em, $10 BB (5 handed) from (Format: Bet The Pot)

Hero ($965)
UTG ($1967)
MP ($200)
Button ($2653.60)
SB ($190)

Preflop: Hero is BB with , . MP posts a blind of $15.
1 fold, MP (poster) checks, Button raises to $40, 1 fold, Hero calls $30, MP folds.

Flop: ($100) , , (2 players)
Hero checks, Button bets $71, Hero calls $71.

Turn: ($242) (2 players)

1. Hero check-raise all in
2. Hero push all in
3. Hero check/fold

I probably should've check raised the flop or lead out.

Floating OOP is generally not a good idea. If you think you have the best hand on the flop its probably better to lead out. Of course if you do that to me, Im going to raise you almost no matter what I have so thats not going to work either.

Being OOP sucks.

i kinda like a CR all in.

check/call is possible but i tend to think it's gonna be hard to get paid. you're pretty much gonna need to hit a non-[d] straight card AND be able to shove the river and get called.

i think you can also 3-bet PF here.

I didnt even think about a check call, the river was the . I agree with 3 bet preflop

My raise to $500 gives me odds of 3.5 to 1 (?) to call his push and I got around a 25% chance of winning by the river

How do you work out how much of a underdog i am if I work out the percentage of the time I win?