Hopeless campaign settings: If by that you mean campaign settings that won't allow any major changes, I stay away from them, both as a DM and as a player. Freedom of choice and potential impact on the game world for PCs and players is central to my enjoyment of the game. You won't find me playing in a Ravenloft game, for instance, nor in a canon Forgotten Realms campaign where the Big Plot and timeline are dictated by the plotlines of novels.
Player-unfriendly settings: If by that you mean settings in which the odds are stacked against the PCs to make for a more challenging game, I potentially like those a lot - if the challenges make for a game with a heroic feel.
I try to use the stacked odds to make the game more challenging and enjoyable. Tricky balance because if the players can't see how to succeed at anything they'd like to do, they'll become frustrated - OTOH if the odds are conveniently lowered or 'forgotten about' by the GM, the game will lose its specialness and you might as well be playing standard DnD instead.
I'm currently running a Midnight campaign (the one S'mon is talking about above), and yup, to clarify my position, I'm one of those DMs who don't rate Midnight among the 'hopeless' settings. In my game I'll definitely allow major changes to the game world. If the PCs survive and grow powerful enough to think they can take on a Night King, for instance, they will be more than welcome.
Some of the stacked odds in Midnight and how I use them:
'Guerrilla'. That's what I thought immediately when I first read the campaign setting. Not necessarily true for everyone out there, but certainly true for me. Broadly speaking, that theme determines the challenges I try to provide: at low to mid-levels, missions that'll take the PCs in behind enemy lines, likely involving combat challenges, and will force them to adapt quickly as the situation changes (or their original information turns out to have been incomplete or plain wrong). This means my game is fairly combat-heavy, and 'mere' survival in the sense of finding food and keeping your head low otherwise isn't generally going to be a main focus of our game sessions.
(In hindsight, I should have stressed that last bit at the outset of my game - some groups play Midnight with a focus on such things and while it hadn't occurred to me, some of my players were also paddling furiously into a 'heavy resource-management' direction until I picked up on that and could take steps to counteract it.)
'Outnumbered'. The combat challenges the group has faced so far have been difficult to deadly. Last session the party of four 3rd-level PCs went up against a vastly superior band of 'gone-bad' Sarcosan riders. If they'd blindly followed their orders (to bodyguard a NPC gnome trader who was going to trade for horses with them), it'd have been a TPK, with the gnome captured and delivered over to the Legates. As it was, they finally worked out that walking a client into a trap wasn't such a good idea. They left the gnome behind and found a way to track down the Sarcosans and wiped out their camp in a night surprise attack, and captured the 8th level leader with only one PC casualty.
'Outgunned'. Fine line that. Midnight assumes that the forces of Shadow are better equipped than the PCs, but in a game run my style successful PCs will overtake NPCs equipment-wise in the long run. After their deserved success over the Sarcosans last sessions, the three surviving PCs are equipped considerably better than suggested MN wealth standards for their levels.
'Last Heroes'. In Midnight, if you don't step on up to be heroes, chances are there will be no heroes left. What the PCs have yet seen of their part of the world mostly looks pretty devoid of hope - I had to provide incentive for players to live up against that, but I refused to give them outside 'hope', such as a prophecy, or being 'chosen' by powerful allies or some such.
Instead I started them out running from orcs and desperate to get through the lines to relative safety in a human refugee camp in the Elven Forest. The commander of the camp promptly sent them off on the gnome-guarding mission - obviously, as one PC remarked, that commander had no one more expendable at hand.
An interim attempt on the PCs' part to ingratiate themselves with the Elves didn't go so well when they unknowingly transported a Shadow device deeply into the Forest, where it might have done serious damage and lastingly weakened the Elves' magical defences.
My success with the Last Heroes aspect varied at first with my group (all seasoned DnD players). Two players took to it immediately, while others had more difficulty adapting and creating their own personal 'bubble of hope' without relying on what NPCs might be thinking.
I love how now after maybe half a dozen sessions, most of the players have developed a sense of heroism all of their own.
'Heroes' Legacy'. This one's actually not stacked against the PCs but works in their favour. (Gotta give them heroes a break ...)
Midnight provides a very nifty (if only half-designed) DM's reward tool in the form of covenant items, basically items with a 'themed' bunch of magic effects that the wielder gradually gains access to as he/she gains levels. The written history of sample covenant items shows that they are supposed to have been imbused with slivers of the souls of former hero wielders. I took that a step further. In my game covenent items can't be Crafted, they can only be found - or may come to exist, or be modified, spontaneously through some heroic act.
One covenant item in my party (a pair of bracelets worn by two brothers) is currently undergoing such a minor change, after one brother put himself forward in the battle against the Sarcosan leader and wounded him seriously before he was killed. I gave the player an opportunity to send 'dying words' to his brother (absent because the player's currently away from town), and will give the bracelets a related new power.
Since putting on a covenant item (or unlocking a new power) tends to trigger stored 'memories' of former users, the PC rogue's dying whisper to keep up the fight will now accompany the new wearer iinto the future.
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