During free roll

Do you put yourself in bad spots on purpose to learn?

absolutely.

Yes.

Yup... If its a really good wrestler I'll give them HG or SC (my worst position), to force myself to get better at them.

Yes

yeah, even though some guys take it personally and then I have to explain what I'm doing...lol

Then immediately regret it when they tap you?

absolutely

Isn't that the point of free rolling?

Yup. Quickest way to learn.