Yeah! It's true that more coin flips means more chances to get a certain outcome, and that the odds for at least one coin having that outcome as more coins are introduced to the flip increases the odds of that outcome happening. On a long enough timeline/enough coins, every outcome is *near certain.
*near because technically every coin flip from now till the end of the Earth could result in a tails, there is no law of the universe forcing a heads result.
That said, the NHL won't last forever (though it is indefinite), and each year that the Wild don't win is another year that no longer counts toward the "flips". In that way, the Wild had their best odds of winning a future Cup in their first season, and their odds have been going down ever since.
Stop reading here if you don't want to read a soapbox stance.
The odds also needs to account for how well-run a franchise is. A team that is perpetually bad would still have poor odds of ever winning a Cup, because even infinity times zero is still zero (in reality no team is perpetually terrible, even if they do look that way on a couple decades timeline). If we want to use the math of odds to our advantage,
I believe (I haven't actually done the math) the best bet is actually doing what the Wild are doing and have been doing: not tanking, being as good as they can be regardless of personnel, and getting as many cracks at the playoffs as possible. Just because they've not made it out of the 1st round in years due to the dearth of top talent doesn't mean they won't win the Cup eventually with that dearth of top talent. It also doesn't mean they will, and that's why the future is unknowable. Outliers happen, and sometimes only outliers happen. That's not a curse, it's math.
Damned socialist hurricanes.