I have no problem with someone upvoting their own comment if it truly adds value to the post and they believe it is important for others to read it. The upvote can move it closer to the top so more people can see it.

What I have a major problem with is someone leaving a comment, upvoting that comment, but not even upvoting the post itself. This is the pinnacle of self-serving Steemit behaviour and worthy of a flag.

It's also a little upsetting to see someone upvote their lame comment, like "nice post." I won't necessarily flag those, but I'd say that's someone worth disengaging with.

Overall, I think it's important to value the financial investment someone has made in STEEM which benefits all of us by propping up the value of STEEM. These people will be mindful of the need to get the best return on their investment. In fact, anyone with an SP balance has a similar interest.

As far as randowhale and boost, I see no issue with this whatsoever. It's simply someone providing a service, selling their voting power.