This is great idea and good questions.
I would think that "leveling the playing field" would be a good motivation for me, if I were the one with substantial SP to delegate.
Delegating for a week at a time is a good start. I know that after I Powered Up, my desire to upvote others made me much busier since with just a 20% vote, I can literally give my "two cent" / $0.02.
Criteria?
I would much prefer someone who does not self-vote much and do not intend to start. This (self-vote), from my perspective, would also include using voting bots to vote for one's posts.
Another criterion that I would use is the discernment when voting - is there a trend of upvoting newbies and someone who does not have much to give back (low SP and low-lower reputation score)?
Last one, and this is optional, is is the voting limited in areas of interest or more generally spread out?
BTW - from my perspective, it will be an added burden to some who is already working hard to give out votes. ;-)
All the best!
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Thank you for the suggestions. I would like to pick people who have similar interests so that that type of content gets supported.