Yes, he should ALWAYS be looking. How to keep season tickets as low as possible for the fans should be keeping him up at night. There's loads of places the club could make savings, it has chosen to mutate into a big corporate monster over the last few years, it isn't a necessity it is what Bloom...
Fan Service.
This isn't Wall Street, not everything has to be considered with an eye on the business, thinking only in cold, hard figures. The germans understand that, it's a shame we don't. It's even more of a shame that people are happy to deride people who understand that.