I do a restart--just like your sample jobs module does.
Is it possible that an exception being thrown in a module's Install method might cause this? If that's the case, perhaps the telerik internal code should re-throw the module's exception, or wrap it in another special ModuleInitializationFailed exception of some sort. A cryptic error related to the route collection is much less helpful.
On a separate but related note, I wish the life cycle were a little more clear. It would seem that a module's Initialize method would be called each time the application starts. And the Install method would be called once--when an admin installs it from the admin page.
I see strange behavior: I can't always get the Initialize method to be called when the app starts. However, both the Install and Initialize method sometimes will get called when I change the StartUpType from Disabled to OnFirstCall.
Could you clarify when these methods are actually called?