Cypress's UI is genuinely good for exploration, I'll give you that. But I've found the debugging story flips once you're past the initial phase.
Yeah, Playwright's headed mode feels clunkier at first. Real talk though: I stopped needing it constantly after writing maybe 50 tests. Once you know what you're testing, Playwright's page.pause() and the inspector are faster than Cypress's UI for me. Stack traces are actually useful when your selectors aren't brittle.
The bigger win: Playwright doesn't lock you into its test runner. I use it with Vitest, get better parallel execution, same debugging tools. Cypress forces you into their ecosystem.
Cypress shines for quick prototyping. But at production scale with hundreds of tests, Playwright's speed and cross-browser support win. Different tools for different stages.