Gundato said:
Benefits may outweigh the risks. If you can make more cash with a bit of risk, it might be worth a gamble.
That makes sense if you're talking about a simple choice like this:
Route 1: 25 gold, 98% chance of success
Route 2: 45 gold, 60% chance of success
But since one of the inputs is the route, it's not going to be like that, because there are numerous slightly different routes. You'd face choices like this:
Route 1: 22 gold, 99% chance of success
Route 2: 23 gold, 99% chance of success
Route 3: 23 gold, 99% chance of success
Route 4: 24 gold, 99% chance of success
Route 5: 25 gold, 98% chance of success
Route 6: 27 gold, 98% chance of success
Route 7: 27 gold, 98% chance of success
Route 8: 28 gold, 97% chance of success
....
Route 42: 45 gold, 60% chance of success
Route 43: 46 gold, 59% chance of success
...
Route 104: 298 gold, 1% chance of success
That's way too much choice. Even if you collapse similar or identical ones, you'd still have to choose between a dozen or so options, for every pair of connected cities.