Dungeon Crawl sucks and I hate it.
Pop quiz, what's better a +4 Mace of Crushing or a +2 Flail of Electrocution? I certainly don't know. I can fall back on received wisdom: generally flails are better because they do more damage by sacrificing some accuracy. Flails and electrocution are rarer than maces or crushing, respectively, so on that metric the developers agree with me that you should pick the flail.
But if you want cold hard math to prove the choice... Let's see, the wiki says Electrocution has a 33% chance of doing 7+1d13 damage, which is an EV of ~5 damage, plus the flail's base damage of 10 gives ~15. A mace has a base damage of 8 and crushing gives it an average of 16.6% extra damage, which is ~9. But just comparing those numbers doesn't take into account the mace's increased accuracy or greater enchantment bonus, both of which are rabbit holes in and of themselves.
And honestly weapons are easier to figure out that most character-building decisions. If I'm wearing armor I have the vague notion I should increase my armor skill. But to what value? What is the specific advantage I get from increasing my armor skill? What is the opportunity cost of increasing my armor skill versus just pumping all my points into my weapon skill? Does the answer change depending on what armor I find? I don't even know where to start when trying to answer these questions.
All of this number munging is so unsatisfying when the result of your character build is completely opaque. The systems are all so... system-y, but you're not given enough information to work them out. Maybe you're supposed to read the source code? Plus there's a lot of luck that goes into each outcome. My best character to date died taking a massive amount of damage in just a few turns. Was my character weak? I don't think so. Was I unlucky? Maybe. Dungeon Crawl has committed the greatest sin of a roguelike: I didn't learn anything from dying.
Of course "character building" is a generous term in the early game. The game trickles out decent items so slowly it's mostly just stalling until you have enough information to make an informed decision, pressing autoexplore and autoattack over and over.
Speaking of which, by giving us autoexplore the game is admitting that dungeon exploring is a fundamentally tedious activity. Many classically-styled roguelikes are similarly culpable; in Brogue it feels especially tragic because the procedural results are gorgeous, detailed and vibrant. It's a stark contrast to NetHack's plain rectangular rooms connected by hallways, but what's really the difference between them when the monsters and loot that lie within is all that's relevant?
The random dungeon is attractive because it foils attempts at memorization. But levels are never meaningfully revisited once explored, so you never get any familiarity with your game's idiosyncratic geography (like you would in Minecraft, for example). Levels are thrown away as soon as they're cleared, thus they have no purpose other than the tactical situations that they create. At the same time they're not complex enough to actually generate novel tactical situations! So yes, it succeeds at foiling memorization, at the cost of being interesting in any other way.
The cellular dungeon is attractive because it results in surprising emergent behavior. But Dungeon Crawl has gone to great lengths to avoid the kinds of surprises that result in bullshit character deaths. In the process it discovered that all the surprises are gone. The joy in emergence is extracted by a carefree playfulness that's antithetical with the lethal experience of a roguelike. When you only have one life you play scared, and any surprise is an unpleasant one.
The dungeon is vestigial and the crawl is tedious, so what's left of Dungeon Crawl?
I still play this damn game every day because it fills its niche so perfectly. When I play games at work I need something that I can pick up or put down instantly as tasks ebb and flow. And as bad as it is it still manages to be an improvement on most classically-styled roguelikes. Its autoexplore and autotravel features sidestep the expected trudge through endless empty rooms. It discourages grinding so fiercely that you are always making forward progress. And it's short enough that an ascension seems within grasp of a pleb like me.
But we can do better. Please everyone, show me your roguelikes.