The people with multiple items are mostly merchants. There are always a few that seemingly have all the luck in drops. I can tell you that I spent a lot on this game already, but I rarely get a good drop. So I seriously doubt STS would have some mechanism in place to reward the ones who spent a lot. Even with shamrock elix enabled, and a LOT of monster bash runs, I still don't have the pinks one would expect.
So basically, it's all luck. I remember being on a dry spell for about 3 months in the past. That was when I farmed daily for hours. I took a break from all the farming back then and decided to start merching to make some gold.
I learned to just play the game for fun and don't even expect a pink to drop anymore. If you don't focus on getting pinks, but instead enjoy running with your friends, it would be much less frustrating, and I'm pretty sure a pink will come your way sooner or later
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