SJ Longthorne

So, I think context, how well you know said person and cultural differences matter a lot. Not being a native speaker myself, I'd say generally means 'in general with no negative or positive load added to it'. I had no idea people could perceive it any other way.

But, why can't it be neutral? If it can be perceived in a positive way and a negative way, maybe the truth is somewhere in the middle?

I don’t know that there is really a universal truth with it being used and received so subjectively. Someone might mean is neutrally, but we can’t guarantee it’ll be received that way. What’s more, what would be a neutral usage?

If I say ‘you’re awesome’, that’s a firmly positive statement. If I say ‘you’re generally awesome’, half of recipients will think you went out of your way to add doubt, whereas half will think you did to to bolster its truth.

Using that example, is there a way that it could be neutral? Any less than positive is surely negative, no? Or maybe that’s just my flawed psyche at play.

I see it this way. Awesome in general is a positive statement, yes. But you could also be brilliant or very awesome. That's definitely more positive than just awesome. So with that in mind 'generally awesome' could go both ways. But maybe I'm being too analytical about this.

so would your argument be that ‘generally brilliant’ is neutral because the tier below brilliant is still good?

Yeah, I guess that's what it boils down to. Generally is dependant on the adjective following it imho.