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Is it acceptable to contract the phrase in the subject the way above (at least in a spoken English) without raising eyebrows?

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    Yes. I'd've sounds almost exactly like I'd have in spoken English unless you're a classically trained speaker with perfect enunciation and/or put emphasis on the space between I'd and have. I imagine you'd raise more eyebrows by consistently pronouncing I'd have correctly with a notable space in between. – Matthew Aug 3 '15 at 20:28
  • :D ok, let's crank it up a notch—what if you saw such contraction in writing? would it be too much? – D4RKS0UL Aug 3 '15 at 20:30
  • It depends on what 'too much' is for you, but I'd say that most people would notice and consider it informal. Writing how things sound instead of how they are written generally looks pretty informal, so I'd avoid it unless you're chatting on the Internet or something. – Matthew Aug 3 '15 at 20:32
  • Informal would be Ida, which is the way it sounds. The final /əv/ in I'd've is largely fictional; in practice it's just a shwa. – John Lawler Aug 3 '15 at 21:40
  • Closely related: Can a word be contracted twice (e.g. "I'ven't")? – Sven Yargs Aug 3 '15 at 22:17
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Using the contraction is a matter of the author's style and the type of writing. It's use is acceptable to reproduce the compressed speech of conversation or first-person narration. From Misadventure: Monologues and Short Pieces by David Marguiles:

Prolly not. (Pause.) Threw me outta school 'cause of it. Least if I'd've been nineteen, least I'd've had a diploma from high school, least I'd've got a real job, maybe. They dint wanna give what you call special attention. Nowadays it's different.

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