JMHO, I think the "Columbus problem" comes from several things:
1. Lack of visibility. Columbus doesn't get lots of national TV appearances. In many years they have gotten only one national game, and usually on NBC Sports. In my recollection, they've never been on the main NBC channel. Columbus doesn't get the big NHL events like the Winter Classic. I believe players want to play on teams that get the big events and national exposure.
2. Lack of playoff success- players wants to go wherever they believe they have the best chance to win the Cup. Columbus, while a playoff team the past few years, they have never been a Cup favorite.
3. Very few high skill players. I imagine players want to play with elite teammates to have the best chance to win. Yes, Columbus has Jones and Werenski, and the goalies may turn out to be high end. That's not enough alone to make it attractive. Put a Crosby or McDavid along with another franchise player like Malkin/Draisaitl and players would want to be there.
4. Jarmo says he is a tough negotiator when a player is under team control. Other than Seth Jones, Jarmo has stuck to bridge contracts for players' second contract. This clearly upset Josh Anderson and I'm beginning to think it's the core of PLD's trade request. There were several contentious negotiations with a number of players: Johansen, Anderson, Bobrovski come to mind, but I'm sure there are several more.