English contractions are very hard and I have been trying to be better at them. For other users like me who struggle with English, text generators like the ChatGPT can help a lot if you ask them to correct for you and they will give you tips. Be careful if it is online one like ChatGPT though, it isn't private!
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I'm guilty of should of, but I usually use shoulda as I tend to type how I talk, and my pronunciation is somewhat lazy.
However I'm of the opinion that as long as the point is gotten across, there is no wrong way to communicate. Alot of people actually say "should of" while speaking, and it only makes sense that they'd type that way, usually without a second thought till someone interrupts a discussion with grammar correction, which let's face it, brings NOTHING to the table.
Have all the things that I of lost, I miss my perspicuity the most.