Personally I think this year will be the worst just because next year you're going to see the fruits of the rebuild start to blossom in both the upper minors and MLB roster. This year, other than probably Moncada and Lopez late this summer, and some fun from Leury and Yolmer and Kahnle earlier, there really hasn't been much to cheer for.
But 100% honest, I thought I'd be over following this team by now and instead I'm finding myself paying more attention than any of the previous last summers, even when the Sox were still hanging around .500. It's just really exciting what Hahn has been able to do. If the Sox hadn't managed to load up on all this young talent it would be different, but man, they are loaded. We'll see how it pans out in the next 3-5 years.