You can't know, but you can guess, based on past experience or logic. The simplest way to estimate the future is to guess that it will be similar to the past.

For example, if you personally tend to write off-by-one errors a lot, it's a good idea to write tests which check that. On the other hand, if you almost never write off-by-one errors, you can skip those tests. If test is cheap to write, easy to investigate, and covers a piece of code that would cause catastrophic problems if it failed, it's worthwhile to write the test even if you can barely imagine a possible situation where it would fail - the degree of the cost matters as much as the degree of the benefit.

You don't "know" when it's OK to nuke a test just as you don't really "know" when it's safe to launch a product - you decide what you're doing based on experience, knowledge, and logic. The important step many don't take is developing the ability to distinguish between good tests and bad tests, rather than simply having an opinion on testing in general.