The implementation is just utterly at odds with the very concept.

You're going Sightseeing. It's free-spirited and fun. You're getting away from the grind to see things that you've never noticed before. Right?

Nope. You're going Sightseeing, but you will never be allowed to forget that you're doing it on the server's terms. It's nighttime and cloudy? You can only get credit from maybe three spots (oh, and you'll need to either guess what our vague clues mean or use a wiki to know which), and if you've already seen those, tough. Better luck in half an hour or so.

I get that the goal is to make content last a while, but making the content this antagonistic defeats the whole point. Only SE could turn Sightseeing into a chore.