[MauranKilom]

That's not the way I understand the "-less" composition they use. "harmless" doesn't mean "poses less harm", it means "poses no harm". "colorless" doesn't mean "less color", it means "no color". And so on. So to me, "suckless" means "doesn't suck", no humility. Admittedly, it doesn't exactly follow the normal composition rules so the exact interpretation is more up in the air, but that won't change the fact that many people will read it the way I described above.

[gpanders]

Well in this case, "software that sucks less" is on the top of every page of their website, so the intent behind their name is pretty clear.

[ydlr]

I think it means both. The ideal is to be suckless, but practically, the most one can hope for is to suck less.