Play A Hand With Me: AJo with a crazy straddle

I play at a juicy $1/$2 live full-ring NLHE game where people frequently straddle to $5, but any size straddle is allowed, so we sometimes get straddles of $15-$25 or more. I am usually one of the tightest players at the table, just choosing my moments while others play crazily, but then the following hand came up:

9 players at the table, UTG straddles to $25 blind and will get to act last. 5 people fold and it comes to me on the button. Here are the four people still in the hand:

Me (on the button): $350 -- generally tight, waits to take advantage of crazy play
SB ($100) -- calling station, not very aggressive
BB ($200) -- fairly aggressive/break-even LAG player
UTG/Straddle ($300 to begin hand, $275 remaining after the straddle) -- insane player who will call with any 2 cards. Tripled up from $100 to $300 two orbits ago with on a 3-way all in preflop.

I look down at

What should I do?

Easy 3bet to 75$

So there's 4 others that limp in $5 now up to you? 3bet $75 will kill the action
I think 3bet $20-30 to isolate one caller which likely is the wild straddle player
Unless you are absolutely sure he will raise then you can wait to 4bet and possible move all your chips preflop

Did you read the same OP that I did? There was a straddle to $25 and everyone folded to OP on the BTN. Straddler is calling any raise. I like $75 or even $100.

no

this is correct

If we raise to $75 or $100, we would expect the blinds to fold all but premium hands and then expect the straddle to call with any two cards. Knowing that, is there any flop we can get away from, or are we planning to c-bet everything? Even a $75 preflop raise puts $153 in the pot on the flop with effective stacks of just $225 left.

Tell us what happened next because that question really depends

I believe you should decide if you want to play for stacks at this time, since as mentioned any reasonable race ($75+) will pretty much make a c-bet an all-in. If you are willing to go with the hand based on your knowledge of the player then raise if not either fold and wait for a better spot, or call (less preferable) looking for a good flop to stack him.

Before we move to what happened next, let me ask one more question: if we're going to be married to this hand anyway and plan to raise and then c-bet any flop, are we better off just open shoving preflop? At first glance this looks incredibly spewy -- throwing an effective stack of $300 into just a $28 pot -- but are we actually allowing the straddle to play smarter if we let him just call another $50 and then decide what he wants to do on the flop?

If you knew that villain would call with any two cards preflop vs an all in then I would probably shove.

As for the actual hand, who says we're married to it? We might have to check back this flop we might have to bet we might have to shove idk, I really would need to assess it based on the flop. Also what kind of person is the villain? Is he more of a calling station but not very agressive or is he always looking to bet or raise?

You can plan on him calling a raise to $75 or $100 in the straddle, checking the flop, and if we check there, he'll shove the turn pretty much no matter what. He might fold to a shove preflop since he has $275 back but he'll certainly call a shove very light (e.g. something like would be an instacall, as would any ace and any pair).

Result: I shoved.

How good/bad was that move?

it can't be that bad if he's as loose as you say he is