I never needed a map in H-town, but in TO the messenger range is fairly large, everyone carries a mapbook. Even if you've been at it for 15 years, there is alway some small residential street or laneway that will slip form memory. You use you map fairly frequently unless confined to the walker zones in the core. The walker zones usually end at College. The transit messengers go much further of course, they'll deliver to the end of subway and some streetcar lines, but they're on foot, so they don't stray far from the subway stop/streetcar route. Bikes end up everywhere.



The 2 largest bike using companies will send people further than in this example of no PS skill, and at any time of year, some companies cut their bikes off at Bloor in the winter, which is lame.

edit- and only dispatch sweethearts get to deliver to the island, it's a great place to take a lunch if there is time. If there isn't time then you don't have to go because the extra fee for the island doesn't nearly equal the money you can earn not going to the island, then they send someone else.