3

I think it's the first time I've ever seen a double contraction like this:

"That’s, let’s be optimistic, a 30 to 50 mile radius at least in which we are the only two people left. I can’t even calculate how many people that means just vanished.” If I wasn’t driving, I’d’ve squeezed my eyes shut and shrunk down in the seat, to try to combat the thoughts this line of talk was forcing into my mind. source

Is this correct standard English?

How does one pronounce that thing?

1

This is a contraction of "I would have". It's normal in writing to contract "I would" to "I'd", and "would have" to "would've" but it's unusual to contract them all three together. It's not necessarily incorrect, just unusual. Normally you'd see

I'd have

or

I would've

I agree with the comment that describes the pronunciation as being identical to

I'd of

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