The Sox have won the WS relatively recently. The Giants have won a couple without a mega payroll. I don't think winning 85 every year is baseball hell. This isn't the NBA. Baseball hell is Pittsburgh,KC, the Cubs.........the Sox are going to need a lot of breaks to win it all, but so does just about every team. Are playoff appearances without a title good enough? I would venure to guess if the Sox were like Detroit and made the playoffs 2 or 3 years in a row and didn't win, it would be referred to as a total fail.
The Sox haven't made the playoffs enough. i would be the first to tell you that, but their philosophy to me seems to be have a top 10-12 payroll and try to put the team they think will be able to win the most games in uniform.
They have expanded their presence in the DR, but that will take several years before any results are seen in Chicago. They picked up Sale in the draft, that seems like a good pick. A lot of people seem to be excited about Hawkins. The system seems to be better than it has been in years.
I think they spend enough money on the major league roster to win. It might not be spent wisely enough to win.