If the items aren't showing up in the dialogue with Gale, then that's definitely a bug - I'd recommend that you submit it to Larian's official bug report form, and attach a save file where the issue is occurring and easy to check/replicate.
You can find their official bug report form here: https://larian.com/support/baldur-s-gate-3?ver=220.127.116.113832#modal
You don't need to do the wisdom roll with Gale at all - I never do, for example, but there may well be an issue with trying and failing it, potentially.
As for the issue with the dice.... there are a nubmer of threads that are quite old at this stage that illustrate the fairly poor quality of the RNG that Larian uses for their die rolling; it's got a visible sine-wave swing to it, if you plot it over many hundreds of rolls, in away that RNGs for other dice-based games do not. It's entirely possible that you ended up at the bottom of a bad downswing right at that moment, and so rolled 1-3 four or five times in a row. it happens in Larian's games more than any other D&D game you'll find. Rather than fix their RNg, Larian introduced Loaded Dice, to offset it. It mitigated the issue enough that few people complain about it any more, at least those who use loaded dice and don't mind being backhandedly called cheaters by the game... but underneath it, they didn't actually fix the problem.