Wasteland 2 is an outstanding example of disappointment. I think the worst thing about it was how you never knew when you were going against a faction until they all suddenly started attacking you and you were forced to reload. Wasteland 3 was very good at least.

Personally, my most disappointing was Red Dead Redemption II. It’s a game that requires an insane amount of patience but there are so many things to do that you begin to stress about the lack of progress. And ultimately the fact you have to do everything a very specific way to satisfy the conditions of quests makes it frustrating. Everyone talks about how the world building is second to none but I guess that means you’d have to want to live in the wild west and for me I get more satisfaction installing a hunting mod in Skyrim because it’s less restrictive over what I can do and where I can go and genuinely has fast travel.