such action undermines the very community he depends on for his survival;

I didn't propose vote buying as a good thing in general, but for people, that are good for the community, create quality content (that is undervalued) and don't overdo it.

That won't hurt the system imho, what destroys it, are whales, that only upvote their own shit-posts, don't curate and don't help minnows.

nothing ever changes for the better without judgements

I'm really not sure about if judging is the root of all evil in first place. I try to avoid judging others as much as I can. Isn't that the whole point of a liberal, free speech network? Instead of trusting other's, I try to develop and adjust my own moral.

Steemit isn't about content, but about making money,

If it wasn't about content and the people, that create it, I certainly would have gone already. Meeting @katharsisdrill and being at Steemfest prooves, that Steemit has powers beyond "making money".

I doubt his buying votes will be of any help

I doubt not doing so, will be of any help for anybody

I would be fine with his leaving Steemit too

This would be a great loss for me personally and for the Steem blockchain in general. So at least, he shouldn't be judged for trying out ways of optimizing his rewards. I won't.