Not if they are your children or if it's written.
You listen to people saying it. The words are distinct.
I don't find it tricky correcting people but I'll choose when to do so.
I've seen 'should of' in an email at work from a colleague who really should have known better and didn't correct him, but my opinion of him went down a few notches.
Had it been in something customer-facing, I would have corrected him.
Accent is no excuse. My grammar is not affected by my accent.
You are making excuses. I am glad my parents and some teachers told me to enunciate clearly.