The source article aimed these questions at "Democratic Socialism", but I think they're good questions for everyone. If you want to read the source article, and it's own analyses of these 9 questions, I've provided the link at the bottom of this post.
1. What is the moral basis for taxing some incomes at higher rates than others?
2. Do we imagine that incomes are entirely the result of some random process?
3. Do we understand that people with high incomes are the most mobile people on earth and that such persons are most able to leave one tax regime for another?
4. Related to question 3, do we realize that governments exist in a competitive landscape, very much like businesses do?
5. Do we have a right to treat wealthy individuals and organizations as a resource for our benefit?
6. Will democratic socialism damage innovation and economic growth?
7. Why do we prize many other kinds of freedom more than economic freedom?
8. Do we really need higher taxes or do we need to rethink the way we spend our money now?
9. Are we getting taxation wrong?
https://fee.org/articles/9-big-questions-about-democratic-socialism/