I've only ever played through Wanderers from Ys III. That shit was hard, but when I beat it back in the day, I felt really accomplished.

In the Tigray Quarry I'd grind till I had like 100 HP. Then proceed to kill the first boss for the Longsword. Then I'd grind till I had enough money for an amulet to use on the real boss. Generally came outta there with around 130~140 HP. Amulet is really the MVP item in that game I feel.

Then in Eldam Ruins I'd grind on the first few enemies repeatedly until level 16 (max level). That sweet, sweet 255 HP would carry me hard, and I could generally afford the Banded armor and Broadsword from the shop.

Everything would feel manageable/easy until Balencentine Castle. Jesussss christ that was a hard dungeon. And the game only continued to stomp me in the nuts from there on out. But I did beat it! Suck my balls, Galbalan!