If the Stars manage to win it all in 2020 they will most certainly deserve it. They will have to go through Vegas first, which I have my doubts on. They feel like massive underdogs there. But their offense scores so much at will that anything is possible - I mean they scored 5 goals in every win in the Avalanche series. Don't think any other team can say that.
Then they will have to face the Islanders or even more likely the Lightning. I think the Lightning win it all. But if you can manage a series win over Vegas and Tampa Bay you went through the guantlet. Could happen this year though, as I think hockey is the hardest and most unpredictable of all the sporting playoffs.
As for the Stars after this run, I have no idea. I thought they were close to needing to tear down and rebuild now, but they are proving me wrong. So currently just enjoying the ride.