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I know that a lot of the time that "Of course" at the start of a sentence will be followed by a comma; however, if it comes at the end of the sentence, should a comma come before it?

For example,

1) It was obvious that I win of course

2) That's the point of course

And so on...
Actually, the "of course" doesn't always requrie a comma at the beginning of a sentence. It does if it's used as an aside. Of course, I could be mistaken in that.

But it doesn't take the comma if you're using it emphatically. Do I think Obama has a chance to win the White House?! Of course I think he does!

I would definitely use it before the "of course" in your two examples.
Yes, add the comma.