I trace some of the fan base issues to TV in the 70's. The Sox were on a bad reception UHF station (44 for us history buffs), then they went to a pay per view service (Sports Vision??) all the while the Cubs were busy marketing WGN across the country. They played during the day and quite frankly some suburbanites don't like to drive into the city at night
Corporate entertaining, when buyers and other executives could get away during the day was nice. Take a customer out to lunch and a ball game.
There was also the threatened move to St. Petersburg if the Sox didn't get a very good stadium deal. Then Governor Thompson kept moving the hands on the clock back before midnight until a deal could be made. IMHO, the Sox would have died in Florida and the Cubs would have won a World Series by now with a $120,000,000 payroll.
The Cell has always been a decent park to enjoy a ball game from the lower level. There have always been about 10,000 excellent seats. The upper deck was awkward at best. The food is awesome in both variety and quality. I have never had a problem getting to or from any event at the Cell or before that Cominsky. I have had a window vroken and stuff stolen at a Bulls game. Someone urinated on my shoe after a Cubs game, oops that was me
And after all that, I would find any excuse to love the Yankees if I was from anywhere within 200 miles of the Bronx. At least heart break happens in October not June every year.