No offense but this was your first mistake. This is WDW. There is some great dining on property but uh. Maybe manage your expectations a bit lol. Nowhere down there is going to be comparable to NYC dining, even the outpost of Il Mulino at the Swan which is far and away the best Italian on property is inferior to the NYC locations.
This is unfair tbh, and I say this as a native NYer. There are plenty of folks here who are accustomed to good non-chain restaurants where they live. And the only thing consistent about Disney dining is its inconsistency. Even outside the bubble, one visit isn't enough to judge the merits of a restaurant because even the best places have off nights. But especially at Disney.
And FWIW, the burger I had at Crew's Cup lounge, which operates out of the same kitchen as Yachtsman, I would actually put on par with the nicer pub style burgers anywhere here in NYC. It's up there with the best I've ever had at home. And for the record the last time I ate at Outback was well over 10 years ago when I lived in chain restaurant purgatory in AZ.