^ I'm glad it's not just me! I was living in Guelph for five+ years, and often cycled over to K/W to 'get a feel for the place', complete sets of maps on hand (including survey and geographical ones), and I'd spend perhaps half hour max most times, then pick the most direct way out of town in exasperation...and even that was a challenge. I'd love to cycle through K/W more, but even the Iron Horse and other trails dump you in areas with no rational way out. It makes London and Paris appear sensible in comparison. If the goal is to do a distant cycle trip, be prepared to take a bus across K/W, or you'll spend the day trying to get out.
I did figure out a way once to the south, on a bridge over the 401 and eventually down to Cambridge on the west side of the Grand River (even Cambridge can be a challenge due to the nasty roads) and the trail to Hamilton, but it ate up valuable hours doing it.
I've talked to many people, and they all agree, it's not easy to navigate. And they've lived there all their lives!