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Political Office for Beginners?

 I'd expect the most common failure mode for rationalists here is not understanding how patronage networks work. 

Even if you do everything else right, it is very hard to get elected to a position of power if the other guy is distributing the office's resources for votes.

You should be able to map out the voting blocs and what their criteria are, i.e. "Union X and its 500 members will mostly vote for Incumbent Y because they get $X in contracts per year etc"

Almost everyone should be less afraid of lawsuits

People are so irrationally intimidated by lawyers that some legal firms make all their money by sending out thousands of scary form letters demanding payment for bullshit transgressions.  My company was threatened with thousands of frivolous lawsuits but only actually sued once. 

Threats are cheap.