It's an admirable thought, but unfortunately it is not always possible. In fact, sometimes it is not even possible on take off, which means we wouldn't be able to ever get airborne!
Whilst it is very true that route selection is important, at some stage it has to come down to risk management. Being in Sydney, if we want to head west we have to deal with the fact that we have to cross the mountains, and there's nowhere to land. If we want to do a Victor 1 or Sydney scenic flight, there is nowhere to land. Even flying up the light aircraft lane to the north, there are times with nowhere to land.
So we can stay local, if that is the preferred option for that particular pilot. There's nothing wrong with that of course. But if we want to go somewhere all we can do is look at the most suitable route, but it doesn't mean within gliding distance of somewhere to land all the time. We need to consider aircraft maintenance, regular emergency procedure reviews, thinking "what if", monitoring instruments, LSALT, weather, alternates etc.
But flying has its risks, and those who choose to do it are often the types who will calculate that if all seems well, the probability of a problem over that particular spot is low enough to be offset by the reward of getting to the other side. That is the spirit of our pioneering aviators we admire so much!