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How are you even supposed to win when they are so many chances to get get nailed with a bad run?!

The idea is that you get good at managing risk. That’s the key thing in this game. Do you take the item that is useful now, but worthless later; or do you take the item that does nothing, but can lead to powerful synergies? The answer to questions like this is it depends on a lot of factors.

I like rogue-likes for the idea of perma-death/rng… But it seems like the game is only scaled for the highest end of heroes and item combinations.

This is correct. You need to find good synergies in order to win. If you have a trapper who can apply the vulnerable status, you want to find ways to deal many small instances of damage in a turn, such as the herbalist’s vine spell. If you have a berserker who deals lots of damage to themselves, you want to find ways to give them shields or self-heal, so that they can mitigate the self-damage. If you just randomly pick things that you think are individually strong, you will struggle.

So many of the heroes are just plain bad, none of their dice sides provide any value.

I think there are almost no bad heroes. They just excel at different things, and like I mentioned above, you need to play to their strengths. Ludus has high base values, so find good keywords to apply to them. Valkyrie can prevent your heroes from dying, so combine that with abilities that “require” death, such as the ghast’s mana gain + death side.

Also, some of the bosses passives are just not fun. Full damage reflection with no cap? If I hit for 20dmg then I take 3x my life total in damage while I still haven’t even scratched the total damage needed to win the round.

Some bosses battles end up with me needing to put in 50 damage total and my damage output is limited to about 7 and the opponents are putting out 26 damage.

The thing is you have an immense tactical advantage over the monsters: You know what they’re going to do, but you get to interfere. Sure, the monsters are going to deal 26 damage if you let them. But you can choose your targets so that you kill one or two of the damage dealers first. Now maybe you’re taking only 13 damage, and you make sure that the ones you take out are the ones that would have killed your heroes. Next turn, you do the same thing, except you still have your full team but the monsters have lost some people, so it’s easier than it was on turn 1.

You have to be strategic with how you play your turns. I mostly play on cursed mode, where you get more and more curses (debuffs) as the run continues. On many turns, if I just do nothing, my whole party would die. But just using the tools available to me, I can almost always figure out a way to keep everyone alive and make some progress against the monsters at the same time. It’s always going to look dire until you actually play things out.

My two tips for you:

1. Use the undo feature A LOT. Play out every turn in multiple orders to see which sequence gives you the best result. As you get better, you won’t have to do this as much, but it’s an incredibly useful learning tool.
2. Think carefully about when to keep and when to reroll. I think a lot of people don’t reroll enough, keeping 1 damage on the gambler when they should be pushing for 2 at least. And then others reroll way too much, trying to get the perfect roll at every opportunity, and then end up rolling blanks.