Some really great ideas were discussed around here on previous threads about stimulating usage of the trolleys. I think its going to be a tough battle to get the public used to them. A big part of the formula is that the demos have changed since those trolleys were introduced. The disposable income available to downtown evening partiers is large enough that they don't look at the trolleys as an option. Simply put, they aren't cool anymore. They go for cabs, limos and party buses or they walk. They do appeal to older folks like me or RA but those folks don't dominate the downtown after hours scene.
In other words they are looking for a red barn with a blue light. To me the trolleys should concentrate on moving daytime crowds and blow off the after 5 business. that was Bill White's model and would truly benefit your business.
Well the "cool" stuff sounds like it's available, so no problem there. I like your idea about the daytime crowds and the trolley. Get that going and I will see what I can do to help. Let me know.