I'm a PO player, and I really have to say that PS Ladder is far much more easier than PO's ladder. Here's why: In Showdown, you do not get to specify the rating of preferred players. That means at the top of the ladder you can be facing the players at the bottom of the ladder.(Not to mention, some pros on a new alt can easily troll the people at the top ladder) Easy as pie. In PO, there's this system which allows you to specify the maximum variation of preferred players on the ladder. Which means if you're at the top of the ladder, you get top opponents!(If you're at the top you'll see many familiar faces)
In Tournaments of PS, this is different. Bad players are eliminated each round, and the good players will have to face off eventually in the finals. This is why Tournaments are more difficult than Ladders... in finals.
However, if you happen to lose to some really strong player round 1, you are obviously unlucky, and probably might have not met this player in ladder purely because of the inability to select similar skill levels of your opponent. Also maybe that player could not be bothered to ladder at all.