Yes, we know today that the Milky Way is a big place full of lights and wonders and that we start each and every exploration trip from a pretty normal, if not outright boring place in the galactic disc. But that was not always so. Back in the 20th century the scientific community based their world models around only one galaxy in the entire universe and the firm belief that Sol was located in the very center. So far, so good, 'barbaric times' you might want to put forward as an argument. Looking back now, 1,300 years later, we allow ourselves to be that arrogant, but we omit the fact that science never was and will be a static thing. It belongs to the Frontier and the new Horizons we open up with each passing day and light year.
It is because of this that the first 'real' waypoint couldn't have been selected at a more ideal point. The Distant Worlds flotilla assembled at the planetary nebula named Shapley 1 (dubbed the Fine Ring Nebula, because from Sol we see a nearly perfect disc/ring). And it was that guy Harlow Shapley back in circa 1930 AD who through tireless observation and calculation deducted that the Milky Way had to be much bigger than it was thought back in the day, and he also found out that Sol was located at a dull spot near the fringe and not, as scientists believed, in the very center. Needless to say, he had a hard time and a Great Debate then about the fuss he created. Essentially, Shapley hadn't scratched at a pillar of the astronomical 'world' model, no, he just kicked it over.
Now, you might say 'Why is Shapley 1 so ideal as a first waypoint?' and I would answer 'Because from here we venture forth to show that the galaxy is a richer and bigger place.' Once again, we are at a threshold to commit ourselves to opening our eyes to the universe and to bring home a new idea of its vastness and beauty.
I cannot think of a better and more symbolic place to start this endeavour...