[rpgraham84]

>The problem is that mapping software is reliable and doesn't spit out a result of what is essentially a random number generator.

Actually, TSP is NP-hard (ie, at best, you never know whether you've been given the optimal route) in the general case, and Google maps might even give suboptimal routes intentionally sometimes, we don't know.

The problems you're describing are problems with people and they apply to every technology ever. Eg, people crash cars, blow up their houses by leaving the stove on, etc.