W&R:SR fits the bill, but I'm not opposed to being a capitalist piggy once in a while either.
Dwarf Fortress is a ludicrously complicated ASCII game where you manage a colony of dwarves doing dwarf stuff like mining, fighting goblins, and going mad only to slaughter your loved ones and make them in to a legendary earing. For bonus points the GUI is extremely arcane and losing due to unforseen bullshit is so common it's considered one of the core features of the game.
I've heard that Banished is challenging enough. It's a medieval village simulator though.
Yea banished can be an absolute dick kicker. Too stressful for me man. Now I play foundation, it’s a similar city builder that’s significantly chiller so I can just toke and vibe while building
Banished is good, one of my favorite town management games I'd say, looks very old school but is balanced well, it's one of the few games where you can easily fuck things up beyond saving if you aren't careful all the way up to the end game vs most similar games where once you pass a certain development point its hard to lose.
Banished is really good, but once you figure out the right patterns the challenge wears off pretty quick. Well worth a play through of the various maps though!
rollercoaster tycoon classic, which is just both rollercoaster 1 and 2 packaged into one game for mobile (works great on tablets), gets pretty tough in the later scenarios
if you dont have a tablet or want to play on PC get Open Rollercoaster Tycoon
Going to reply just to recommend open rollercoaster tycoon. Get rct2 and open rct. You can find the original scenarios for the game too. That said I personally don’t think it’s that difficult overall. And you can easily cheese the harder scenarios
management rather than tycoon, but frostpunk can be properly brutal (and its also really good)
The new Beaver based game Timberborn is pretty solid on this front. Gotta survive droughts instead of freezes and you have tools to control water flow
Other games in the genre I have in mind for people who are interested but aren't me:
- Cities Skylines: Really easy so the opposite of what I'm looking for, but a lot of fun to play around with.
- Frostpunk: see other comment
- Prison Architect: a bit tricky, and kinda fun if you reorient your as a minimum security re-education center imo
- Planet Coaster: The scenarios are fun and get progressively more difficult, lots of room to be creative with all the theme park decorations
- KSP: Very hard, something like this is what I think I'm looking for, although I'd rather have the challenge be in economic management rather than aerospace engineering
- Factorio: Haven't played in a while, maybe this would scratch the itch
- Airport CEO: Downloaded it based on some meme Youtube video but only played it a couple times. Idk if it's been updated, but maybe it actually went somewhere
- There's a bunch of airline manager sims online, and that would also be a lot like what I'm looking for, except I want to play something that actually resembles a game with spreadsheets in it rather than just a spreadsheet.
In short WR:SR is probably the ultimate suggestion for this, but I just wish it had a bit more "polish" (not to be too greedy about it or anything)
Factorio can be a good pick if you have someone to coop with on deathworld. I must have spent a couple of months trying to perfect a run on that mode with friends.
RTC is a weird game when it comes to difficulty. Cheap, spammable designs are just way more efficient than the bigger rides, and so the ‘optimal’ playstyle is kinda boring.
There are a few standout scenarios that break away from that formula, and that’s where the game shines
In X-Com you have to manage a secret government anti-alien agency that is constantly underfunded, under attack, and under severe staffing pressure. There's also a new Xcom which is okay I guess.
Xenonauts is a good remake in style of original X-Com, but during the Cold War. It's very good.
I see you like KSP, but wish there was a version more about management - I give you Buzz Aldrin's Space Program Manager! In it you play as either the head of NASA or a high ranking Soviet official or the leader of a fictional "Global Space Agency" and manage your way to the moon. Includes a ton of missions that were proposed but never actually flown, so you can explore some alt-history like actually building the Dyna-Soar or the N1.
Offworld Trading Company always looked like an interesting one. I've played it a bit, but not sure I can say if it fits what you are looking for very well.
Kerbal Space Program with the RP-1 mod.
The stock game's "tycoon" aspect is very basic: Do contracts for funds, spend funds on rockets and facility upgrades to do more contracts. It's not very deep and the gameplay focuses primarily on designing ships and flying them.
RP-1 introduces research time, construction time, rollout time, launchpad reconditioning, astronaut training and retirement, tooling of fuel tanks and avionics, and engine failures. Makes planning just as important as flying.
It also puts you on Earth though, with historically accurate rocket engines, real fuels, a more brutal (but more accurate) flight dynamics model, speed of light delays on radio controls, etc. It takes more delta-v to get to low earth orbit than the pluto-analog in the stock solar system.
The problem I have with KSP is that I take a very difficult game and can't help myself but to turn it to 11 by enabling every realism mod I can find. Still fun, but I get exhausted quickly.
RP-1 is a great recommendation because it is basicaly a huge modpack already containing everything you need the only thing you might add is some historical part mods on top.
I get that "add every mod syndrome" from Skyrim/Oblivion days too, but with Kerbal compatibility is much less reliable and in this case if you add additional realism mods it wont even load probably.
Railroad Tycoon 2 and 3 had some challenging scenarios. Both are also capitalism simulators.
Oxygen Not Included? Space colony survival sim, mining, etc.
Once you get the hang of it, just keeping a colony alive isn’t too bad.
But when you gotta get heavy industry up and running and do all sorts of arcane stuff to manage heat, I think it gets pretty difficult in a good way. Your first cooling loop to make liquid oxygen is quite the experience.