Steak is amazing when properly cooked and seasoned (salt, pepper, garlic powder). If its chewy its likely a cheap cut, cooked too long, or cut the wrong way (cut against the grain, not with it).

I used to be picky too, I learned it from my mother. At some point I realized that if a restaurant is serving it, that means people are buying it, and its worth trying. It turns out that most food is delicious, even if I think its a little weird at first.

Your uncle sounds smart minus the 3 boats (unless he uses them for business purposes)