I find it to be even more unsettling when people of sufficient wealth do it, knowing damn well that they don't need it as much as the others commenting on their posts. 

I used to get so frustrated, actually I still get a little pissed when I write out a detailed comment to an article (such as you have done here),  get a response from a whale/high rep member and the the dick upvotes their response bu leaves me with zero. It would be like if I upvoted "this comment" and ignored yours that prompted me to write mine. I find that to be quite the dick move in most cases. Let the guy behind you upvote your musings if they are of sufficient quality that they warrant it. 

I also hate the buy a vote bullshit. If I can write a trash article and simply buy votes for it, how does that qualify as the community picking only the best content. How does that inspire me to get my shit together, improve my skills and pick topics of interest?. How does it motivate me to engage my audience, interact with them, know them and help them so they help me? If I could just buy votes up to appear popular I would not have the need to know people. It become non personal and just a sham site full of shit masquerading as a place where the community decides the best content. 

Remove the self vote and the bots and I think we would see many the milk the system move onto other things and many that are unnoticed would get noticed... here have .03 :)