I still find it pity that my upvote isn't equal for anybody. An upvote with the same VP% has easily twice as much value when upvoting a post which did pass the reward curve than on a post which doesn't! Feels strange!

Yeah. It sucks for small accounts or those whose posts usually never break the reward curve. I think the majority of people on steem will just go for low hanging fruit and upvote those who consistently make the trending page. I don't think this is good for the long term health of steem though if everyone goes for curation maximization.