How do Pilots Actually Setup a Flight Plan?

Honestly automation does a lot of the work. I use ForeFlight, and when you put in a departure and a destination it gives you suggested routes. Some pilots fly everything direct, I find that to be just lazy and not the most efficient or safe way to plan. Basically it depends on the capabilities of your aircraft, the weather, the terrain you’re flying over. If you give me a few example trips I’ll tell you what I’d do.