What result would have met your test for worked out? Gambling with taxpayers money is a pretty good description of the job of government (will this transportation system get used (consider Detroit's highway system)? Are we encouraging business the right way? Will this law reduce crime?)
Uncertainity about the usage of a hypothetical transportation system is qualitatively different than investing money to a company that has been mis-managed so badly it's going bankrupt.
(2) Even if it had, "it worked out" isn't a good justification for gambling with taxpayer money.