Don't speak ill-will of anything or anyone in an interview, it's not going to bode well for you. At a minimum, people don't want to work with people who focus on the negative
I have the same opinion. I don’t see the value in having this discussion in an interview - save it for your blog. That being said, there definitely is value in being capable of discussing type safety as a tradeoff when making architecture decisions, I don’t think anyone competent would argue that there are zero scenarios where type safety is part of constraints/worthy of discussion. And OP has some great opinions about this, given they have actual experience in a project where that had to be addressed, which gives them context about a problem their colleagues might not have (which is why we hire people).
Depends on how hard you need the job and how you tell it.
If you see the interview as on equal footing (they want to learn whether you fit the job and company, you want to learn whether the company and job fit you), you can be a bit critical.
You can do that without being negative, though. Knowing of a rough corner in their startup, you can ask “How did you avoid running into Foo?” or “how did you find time to move to 100% TypeScript?”.
> people don't want to work with people who focus on the negative
This is true. And yet, those who focus on the negative are the ones who are responsible for the most significant improvements because of their lack of complacency. But in the context of corporate software engineering, who cares about significant improvements? Not me!
I would counter that those that make the most significant improvements can see the gaps, but focus on, and communicate effectively, the opportunity rather than being complainer. I think we will all agree the workplace is as much politics as it is technical prowess
I tell every person that I interview both that I want to hear their true opinions on technologies and tools that have worked favorably for them as well as technologies and tools that they were disappointed by.
Anyone who has ONLY favorably opinions of the tools and technologies they have been exposed to probably has not been working in technology for very long at all -- or they are afraid the interviewer will think poorly of them, which is regrettable in my opinion).
People also ask "what is your greatest weakness?" - good luck to anyone thoughtful enough to know a real answer and thoughtless enough to tell it honestly. That interview question is fair but there is a decent chance here that it selects for people who are good at answering hard-to-answer questions more than anything else. It pushes for someone who can fabricate inoffensive but plausible answers.
Selecting people with high verbal and social intelligence isn't a bad interview strategy though.