Ain't that the truth. My grandfather and father were both born and passed without seeing their Cubs ever win. I'm in my 30s and I'm starting to question if I'm generation #3.
I don't think it's a big deal if there Wings never win again. It wouldn't change my life much, if at all. But it would be nice to see them put a focus on more aggressive moves to improve, as that's a more entertaining product. And after all, this is entertainment. No different than Game of Thrones or a Broadway show. We invest our time and money in the hopes of having fun watching skilled performances.
I also very much enjoy the community aspect of sports, thus my participation here.