Pittsburgh does a decent job with their stadiums and city planning and bringing in revenue. They use the Penguin's new arena, PNC field, and the big ketchup bottle to host many events throughout the year. They also have a beautiful Casino (hate to admit, but much nicer than the Horseshoe) close to the Baseball and Football stadiums. Also, they have Peterson Events Center, which is owned by U of Pitt, but brings in events as well adding to an already booming Oakland business area which is basically on the campus.
Cleveland lacks hockey, and attractions for the younger population, including College students. Plus, Cleveland State is not a large enough school to help fill these big venues and events. Many people who go to Cleveland Events drive from East/West Cleveland, but the majority have to travel farther to get there and the City is not very commuter-friendly. Not to mention, Tower City has turned into pure garbage which makes it less attractive to the outsider who might want to spend a weekend in Cleveland.
I hate to admit it, but I know I have more options for my entertainment money by visiting Pittsburgh. Cleveland needs to step-up the Major attraction venues and create an entertainment district that feels fun and SAFE. Even the Horshoe, I hate walking past multiple homeless people on my way to the door. This city needs cleaned up all around before we can even look at the Browns Stadium adding any revenue.