Prehand Descriptions
Villain 1: extremely loose preflop (enters like 90% of hands), gambling attitude but seems to be able to get out of tight situations, not easy to read based on body language, does not play on mathematics
Villain 2: total loose-passive fish
Hero: fairly tricky player, tight-aggressive, known to pull large bluffs, understands theory and math

$.25/.50 NL (7 handed)
UTG V1 ($40)
EP ($10)
MP V2 ($20)
LP ($20)
Button Hero ($45)
SB ($80)
BB ($5)

At our game, we allow straddles and restraddles from any position. There has been straddles for most of the past 5 or so hands. For this hand, button hero straddles $1 and UTG V1 restraddles $2.

Hero is dealt 7 7

EP folds, MP V2 calls $2, LP folds, button Hero calls $1, SB BB fold, UTG V1 checks

Flop ($6.75) 6 5 4
V1 checks, V2 checks.

Hero?

Raise pre

why are you not raising pre?

AP, bet $5+ on the flop.

I would have usually but from past experience, I know that V1 would call any reasonable raise preflop if he already had money in the pot. And postflop, unless 3 small cards came up, I would have no idea where I stood because I do not have a good read on V1. Basically, I didn't want to build a big pot when I wouldn't know where I stand.

I'd raise preflop and bet something like 3/4 pot on flop

Playing scared poker will not make you money. You have the best hand more than enough against V1 to raise for value/iso limper.

Raise and play some poker post flop. If he calls any reasonable raise, make an unreasonbale raise and iso limper.

These two sentences seem to contradict each other. If you know what he does pre, you should have some read on him.

And damn handsome too!

Pot the flop.

so shove and print money.

Why thank you!!!

But seriously, it seems like the consensus is a big preflop raise followed by a postflop 3/4 pot sized bet. As an afterthought, this seems like the best course of action.

What actually happened postflop was that after it was checked to me, I pushed all-in. My reasoning behind this was that I would get called by TPTK, pair and straight draw, etc and get paid off. Also, there was not a single turn and river card I would be comfortable with except for a 3 or 8, so I wanted to bet real big to shut others out, especially V1 who likes to chase. After I pushed, V1 calls me with 87. He flopped a straight, and the turn and river both missed me. I know V1 got damn lucky, but was my thought process right?

Ever hear "don't go broke in an unraised pot"?
Raising pre takes most of this out. If it still happened, only then do you get to bbv it lol.
You only have 45 in a straddle restraddle pot so.... Make a big enough raise pre to have an SPR that plays well post flop. Try raise to 8 or so. Then on the flop you stack off with pride and a damn handsome smile. This is kind of short stack 101.

Wow I feel like an idiot now. Forgot one of the most basic sayings in poker. The only reason I pushed was because I knew that I was better than most of V1's calling range. I was hoping for a call. Preflop raise followed by large postflop bet definitely makes much more sense now.

bet something bigger than half the pot

As others have said... raise pre. C-bet the flop, dont play scurrrrred your overpair is likely the best hand on that board and if it's not you got outs!!! gogogogogogo