Me and villain have a lot of history, I would label him weak reg, but in the previous session, i triple barrelled him on a 423JK board and he called me off on the river with A2s

6 handed
1500 effective
1/3 game with villain straddling to 6, I'm in CO with A3o, i decide to open because i want to play pots with the straddler
I open to 20, BTN calls SB calls and villain in straddle calls
Flop is Q5Qhhc, checks to me i bet 50 (I have the A of heart), everyone folds and only straddler calls
Turn is Q5QK (hchh) completing the flush, he checks I bet 200, he calls
River is a brick Q5QK8, he checks again and I decide to turn my hand into a bluff, I bet 1000 on the river, villain goes into the tank...

I know my preflop open is very loose in this situation but it is because I really wanted to play a pot with the straddler, besides that, what is your opinion on the hand? Should I be turning my hand into a bluff?
Feedback is much appreciated

Preflop logic is lolbad. First, there are three players between you and the straddler. Second, why do you want to play a pot with him? Your hand sucks and needs to rely on fold equity postflop to profit. But you just said he called you down super light. So the play makes no sense.

As for post, what do you think he has when he calls the turn, and why do you think he will fold otr?

Definitely not trying to get someone off a flush or trips at these stakes and it seems especially bad given your history with this guy

Thanks for the feedback guys
I feel like I played this hand very badly on the river
After he calls a huge bet on the turn I should be shutting down
Big mistake by me

The SS Spew immediately sunk after leaving port.

Did you learn nothing from the A2 hand? Having the A makes this not pure spew, but this is bad given this V.

Pre is really bad... stop making excuses to play hands because you’re bored.

Flop is spew too vs 3 other players.

The turn is okay vs most players, but given he called a 3-barrel with bottom pair, again spew.

River is spew again. Dont try to get fish to fold big hands in poker.

Nope, I would fold pre as well.

Ya, I don't like this hand at all.

Once he calls the flop, I'm completely mentally out of the hand and ready to insta-muck.

The flop and everything afterwards are pure "steal all the pots" syndrome, you gotta just let this one go four ways.