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Originally Posted by 44 AMP
No.
Because you are not paying the sales tax on your speech, you are paying it on the buying of the leaflets. No matter what the leaflets said, you pay the same tax. Not a free speech issue.
Now, if you were taxed specifically because of the content of the leaflets, that would be a free speech issue.
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While not disagreeing with your conclusion or reasoning, this may show up part of the imperfection of reasoning by analogy. Certainly what you describe would be a free speech issue because it would be a content restriction, but that is something peculiar to that specific right.
What if there were a $100 tax on sheets of paper and all emails without respect to content? Do you think that difference might abridge the right?