Well mine broke at 32K. When I bought the bike it had 28K, I had not really done much with it yet at that point. Mine broke cleanly and when I inspected it after the break, other than the place where it no longer connected to the other end it looked great. So I am not sure an inspection would have warned me. Thinking back on it a couple of times before it broke I think I heard it squeal. So It may have not been adjusted properly.
As Pop mentioned unless you live in a big city where they have a big Victory dealer, you will be looking at a week or so before getting a belt. So the question becomes do you want to change it when your ready or when it decides to break. So having a spare around is probably a good idea if you are on the upper side of the mileage limit.
2013 Vision Sunset Red - Stage 1 exhaust, VictoryHID Cyclops
2004 Kingpin - Traded