The more I think about this, the more I fear it is flawed a concept given that there will always be those who gamify any system as soon as they find a loophole.

The loophole here is that somebody will just create a farm of upvote accounts. And of course, there’s voting trails. Long term a whale will not be interested in discovering the good stuff anymore if they see that their search for quality content written by less popular authors (sorry, there’s so much not popular enough quality content on Steem that the game isn’t all about minnows) is constantly rewarded by zero because of voting trails diluting their possible chance to win. Which seems a core idea in the reasoning behind this idea.

Why wouldn’t a whale just delegate away then? No matter whether for profit or to other curators.

Make it a game, fair play. But don’t overreason it because the more you try to reason things, the more obvious loopholes become. This won’t fix voting guilds/trails, only if the original upvoter gets a higher chance to win. But that’s hard to determine. Not every app can be obliged to open up an API, and any pattern recognition algo may be too resources hungry. Whales will still have their trail because they still open up the highest rewards, so the argument that they will want to find less popular quality content because of less competition is an oxymoron, almost.

Of course, there’s always the option to devaluate the value, and rewards, of automated votes by implementing a dual citizenship structure in which apps must identifying as such,. Failure to do so may result in a whole account (with whole wallet) being frozen, locked, and eventually deactivated.

To be honest, the evolution to such dual citizenship structure is the only way to ever possibly start tackling whichever form of automation is loathed. At the same time it would also introduce an option to completely freeze an account, something which as side effect may become handy a tool for bodies such as steemcleaners. But that also requires rules.