Its like sometimes we forget that the 31 other owners are very smart people, who also spend a lot of money, hire hockey people, and want to win. Its incredibly competitive and just doing everything the right way doesn't even remotely guarantee you'll actually win a Cup. It also takes a crap ton of luck, in addition to doing literally everything right, even down to finding the right 4th line grinders in the dumpster bin to fit perfectly into a locker room and on the ice (think DSP and his 2 months of incredible value sandwiched around a year and a half of absolute nothingness). Oh, there's also timely injuries, or as I said, incredible luck.
I love Ted and I have serious doubts any other owner would do better. The Penguins were absolutely gifted Sydney Crosby in a complete scam of a one time lottery rules change after the lockout. That should have been our 1OA pick, but instead the Pens got two 1OA and two 2 OA picks in four years straight. They don't win a single Cup without those gifts.
It takes luck, and skill and its still incredibly hard to win a Cup.