I just go by gut feel. We are fairly practical, so if something won’t bring me value, I don’t feel the need to pay for it simply because it’s “nicer.” On active vacations we don’t pay for fancy hotels. But we do pay for good excursions and activities. On relaxing vacations, I will pay up for a nice resort knowing I want to lay by the pool or beach with a drink.
We don’t upgrade the type of seats/cabin on flights but I do pay up for nonstops and better flight times whenever it makes sense. (I wouldn’t pay double or anything, but a little more, sure.)