The hardest part about getting a whale vote is not getting one the next time.
Exactly! Because even if you encounter a good post of one author once, it is really difficult to come back to everyone and reads all those posts. Simply... there is too many of them!

But if a voting power will be spread among 20 trusted experts... there is much higher chance that one of them will come back next time.

Then you know of other little guys who are in the Whales circle. They continue to get the vote even for some little post of really little value to many people. (again my limited view)

From my perspective... this looks exactly the same. But I do not believe whales are doing that on purpose... in my opinion many of them are doing that mostly because finding new good authors is really hard.. so they prefer to avoid the pain of looking for... and they decide to reward an author which they know, which is above average.

But this is a problem, because this author have less and less reasons to produce better and better content... because he gets rewards anyway. That's why I do not like an idea of auto-upvotes.

It would piss me off and probably other people too. The thought would be why do you let someone curate that upvotes things you do not agree with?

I agree with that. But once again... this is an option, which nobody have to use knowing what a reaction of people can be. But in my opinion, this is nice to have feature.