In my real life, I've negotiated many union contracts on behalf of my company. Some have been here in Winnipeg, and some out in B.C. Some negotiations dragged on for months, and some got settled quite quickly. Generally speaking, if both sides come in with reasonable positions, and listen to each other's concerns, solutions can be found quickly. At the end of the day, both parties have more in common than have in opposition to each other. The difficulties lie when someone's ego takes over, or they dig in their heals to "win" the argument regardless of the long term result. So long as they stay focused on the big picture of growing the game, attracting fans, and putting a quality product on the field, while remaining fiscally prudent, they will get it done. If it boggs down into "More for me and less for you", then their will be problems.
Some of the best results, for both sides, have been reached in contracts that we've settled in 1-2 days. It is folly to think that longer negotiations really achieve more in the long run. That being said, each negotiation is unique, and I fully appreciate that there can be sticky issues that need to be resolved.