no, you're not. its not being a loser to feel weird about flagging. however, keep in mind, that's what flagging is built into the design of this platform for. to flag posts that you feel are not valuable. it costs voting power to flag. i don't know if you get that voting power back if you unflag. so, if you spend the voting power to flag, maybe don't undo it. it's not like you are flagging to be a jerk. you are flagging because they earned it haha. also, im not exactly sure how steemcleaners work, but they can somehow be summoned to posts where there is suspected abuse such as spam or copy/paste/plagiarism.
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You are right - I checked soon after flag/unflag actions - it counts as TWO votes. He deserved one downvote I gave him two and spent 2 votes myself. What you said makes so much sense.