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I have trouble identifying when to progress into the next zone and the punishment for doing so too early, or having a build around luck where random loss is part of the build, is very harsh.

The game is meant to allow you to meaningfully impose your own playstyle on to the characters, but unfortunately, not to the regard that you might be hoping for. 

Your experience has been heavily negatively impacted by your stat allocation. The first Character is all about having great defensive stats as she has lots of armor. As a tradeoff, she doesn't get much luck or agility. You can see how many stats you get per stat point in the Extra Info section of the Stat Allocation menu. Characters are partially bound by their inherent weaknesses and strengths, making your playstyle hard to pull off on the first Character.

Additionally, the problem with your allocation is that Agility and Luck are only as powerful as your Attack Stat. Agility gives Combos, increases Crit damage, and Luck increases the chance for those Crits. This synergy where Agility and Luck and Attack all benefit each other means you can't skip out on Attack.

With just a dozen or so allowed fights (unless slightly modified by equipment), every loss in a playthrough hurts very much, especially when the level-up curve is so extreme (which I generally approve of!).

You get almost 50 Encounters by the end of the game because defeating a boss gives back Encounter Points. To get to that point though, you need to have a somewhat appropriate Allocation spread.

For the equipment, some random-stat dynamic equipment may help lessen that issue (Diablo-Style)?

In a way, this already exists. You are meant to have the ability to get all non-accessory equipment slots unlocked before the first boss. And each equipment type specializes in a different stat. Your weapon gives Attack, your armor gives health, your shield gives Defense, your helmet gives Luck, and your boots give Agility. This way, you'll always have a little bit of everything.

I can only really see your Allocation spread working on 2 out of the 8 planned characters. And I want to keep it this way. You are meant to be able to strategize to bring out the strengths of your characters, while also bringing into consideration what your power fantasy is. The problem is that you can only do that to an extent. Making it so that you could do whatever you wanted Allocation wise removes a core part of the strategy of this game.

Thanks for the feedback! I'm sorry that your playstyle doesn't work well on the first character. But because many players like the game for very same qualities that make you dislike the game, I'm afraid I won't be changing this mechanic.