The problem is of course the new annual revenue is far from guaranteed. I am not saying it shouldn't be done, but it should be a strict business decision not a "vision". For example, while developing the waterfront can generate future revenue, so can building multimillion dollar condos there and turn the entire thing into a concrete forest. Given the location and the view, I'd say the condos would be a far surer bet and the city probably doesn't have to spend a cent since private developers will fight for the land. Is that good city building? Probably not. Does it make more financial sense, probably yes. (I am just saying this as an example, I didn't do the cost/benefit analysis to be sure.)
Another example would be the new homeless shelter. Some people argued that helping people back on their feet will generate future revenues for the city, so it's worth the $11.5 million. However, if you treat this as a strict business decision, you would see that it's probably a very risky investment with very little chance of positive return. It might be the "right" thing to do, but it's not a good business decision.
A boring and uninspiring leader does not mean he would do nothing. It only means he would not let his "vision" get in the way of making objective business decisions.