I have seriously considered running a bot that would flag every post on Trending. As you say, it wouldn't be personal, it would be money, because it would apply equally to each post as a function of its reward.
One reason I haven't done it is that I am largely unconvinced that the shape of the payouts is objectively bad. Flagging those top posts would send nearly all of those reduced rewards to a slightly larger set of moderately voted posts. The posts at the bottom with no votes or minnow votes would still get nothing. So even if you believe that it is a good idea to reward unpopular posts merely for the act of posting, this doesn't do it.
And frankly many of those most rewarded posts are doing good things to help develop Steem. They are more talented posters, open source projects developing for the platform, curation guilds, highly participatory games (yes, I know this is controversial, but I believe they are a postitive), positive black swan posts from new/unknown posters who hit it big, etc. It is not at all clear to me at this early stage that spreading the rewards thinly in a largely blind manner on random content just to be "more fair" actually will help invest in and grow the ecosystem in a significant way.
I have run a bot which randomly votes on arbitrary posts and comments (with enough vote power to generate a payout). I did this in part instead of focusing on Trending even though I was well aware it was less effective in terms of dollars moved, specifically because I wanted to move (fewer) dollars all the way to the bottom (perhaps encouraging people who otherwise get nothing and be more discouraged) and not just take sides in the contest between the Steemit "millionaires" and "billionaires" (figuratively speaking of course).
Still, it was entirely speculation on my part whether sending dollars all the way to the bottom is actually a useful thing to do anyway. It is easy to look at someone developing a mobile app and receiving funding for development from highly-voted posts and see that it helps the platform. (I made similar comments about cutting witness rewards because I knew how many good projects clearly adding value to the platform were being funded that way.) It is less clear that sprinkling a small amount of rewards widely really is useful whether or not it is "fair". But that doesn't mean it necessarily isn't.