It is not uncommon for people to win a reward higher than 50 sats. People post proof of 500 or 5k wins a few times each week. We even see people winning golden tickets. It is only the top 3 prizes which we have not seen any proof yet but the odds are so low to win them that I would be surprised if an active forum member has already won them.
I think winning 200 dollars thing is about the similar way, it is not very common and I hardly ever see anyone win that. However there was (I don't know if that is still going on) some sort of extra reward for anyone who get 200 dollars and then share it on a specific topic about it, people came in and showed proof of them winning the 200 dollars and they get extra reward for that, freebitco.in is a website that may have more users than bitcointalk overall let alone having all their users here, so that means they pay people extra money to start a new account on bitcointalk just to share proof.
If they wish so, or if the public really wants to, they could do something like that for rolex winners as well, just pay them some extra money to come and write here, hell even do that for lambo winners, I know one was a user here but for future both rolex and lambo winners could be paid extra to come here and show proof of receiving the reward. I trust them though, I do not need it.