I never thought that these two could be pronounced the same.

Yes, English spelling is very misleading.

I pronounce of as in office

That would be a mistake in all dialects of English. It is always pronounced with a /v/ sound and the vowel is a schwa. 've is also a schwa plus /v/.

Jesus Christ make it stop.

It’s because “should’ve” and “should of” are pronounced the same. It doesn’t make sense because they’re just writing what they hear instead of thinking “I’m using the contraction of the auxiliary verb ‘have’”…

“Should’ve” and “should of” are pronounced the same, what are you talking about? There’s no way you can mix them up in speech. Are you even a native English speaker?

They use ‘of’ because they don’t understand (or pay attention to) the grammar of what they’re saying.

Sure. Because it sounds identical. " 've" and “of” are both pronounced /əv/, hence the confusion. Native speakers write what they hear. If you ever want to stop errors like this, the only solution is spelling reform.

Shakespeare did not “make” changes, he’s just a very good record of changes that had taken place.

I miss it. There’s just not enough people here. Refreshing doesn’t bring hardly anything new, none of my favorite communities exist, and where they do they’re so small that nothing gets posted for an entire day.

I mean, I know these things take time but I’m pessimistic.