Real world procedures?

And, I imagine, a RL pilot would almost never take off VFR for a 500 nm flight in a Caravan. Fuel is free to me, and I suppose if I wanted to stay VFR I could have just magically dumped more fuel in the plane and stayed at 3500 for the whole flight.

I’d guess close to 100% of flights like this in planes that want to be at FL100 are flown IFR regardless of weather.