When someone downvotes me, that's money that I planned on having when I made my investment strategy being taken away.
That's generally not a good strategy in terms of investments in general. Expectations typically come back to bite you when they aren't met.
If people were more liberal on flagging, it'd make everyone more hesitant to post.
Which is not necessarily a bad thing. It reduces spam and like you mentioned probably increases the level of quality of content on the platform. Which benefits everyone in that creators produce better content and consumers have content more worthy of their time.
I personally only think flagging should be used for spam and illegal activity.
A lot of people also think this and thus mediocrity thrives. Because most people don't make value judgements, they simply don't want to offend people. But value judgements are one of the greatest gifts this platform gives us.
I think that if we simply discarded the pointless reputation system which impacts visibility, flagging would come with less detrimental consequences and people would be more open to it.
You missed my more important note on the second quote there, which is that fear/anxiety over if people aren't gonna like your post "enough" for it to be worth posting wouldn't really mean more better posts, but probably less posts and less posters. You can't drive adoption when people will just bully people off of the platform, and the only reason people are here is for money, otherwise they'd go to tumblr or twitter or whatever.
If you are flagged, the worst case scenario is that you earn the exact same amount of money for your content that you would otherwise earn on some other platform. What is to fear? Not earning some arbitrary amount of money that people think they should earn?
Sure, but that doesn't mean that those people are entitled to that money. The way that people expect this whole social experiment is backwards from how it should run. There is so much focus on the content creator and their personal needs rather than the content consumer and the value their attention brings. You need good content to attract people like that. Once you have a consumer base, then creators have people to grow their communities. But for now, I don't feel that dissuading the (money or else) types isn't the worst thing.
Yeah, no one really deserves anything, to be honest. But, again, if you're not making money, what other incentive is there to use steemit instead of other blogging platforms? Most normies don't care about blockchain tech and anti-censorship stuff, but that's a decent plus-side for me on a personal level.