How can I resolve a repeatable skill check when there’s no time constraint or clear drawback from repeating it? [duplicate]

Willem Renzema’s answer to "Can you Investigate the same room twice?" and abalonemacaroni’s answer to "I failed to open a lock. Now what?" seem to lean towards the idea that if an ability check can be repeated indefinitely given enough time, a drawback should occur on each failed attempt to offset that.

But how can I resolve a repeatable skill check when there’s no time constraint or clear drawback from repeating it?

For example, making a History check in a library, lockpicking a safe that you’ve already stolen and brought back to your hostel, or making an Investigation check on an emptied dungeon, etc.

Basically, it feels like they are going to succeed in both cases, and the roll looks useless.