Nothing wrong with country road without shoulders ... most of my riding has been on that type of road.
So now I'm wondering: how many people here basically bike where they want to (within reason), without thinking too much about the safety of the route? -- yup ... I ride where I want!
Do you simply bike and expect that motorists will pass you as they can? -- yup ... and they will. It is too messy and a big hassle for them to run you over.
There's a ride I'd like to do that takes me along roads that are somewhat windy and hilly, without much shoulder, but they don't have a great deal of traffic, so I'm tempted to take them. -- go for it!
or do you just get out on your bike and hope for the best? -- most of the time. That's a great way to discover new routes. I also use maps.