@Smokin Joe
Not a good analogy. Traveling to distant planets is a whole lot more complex and expensive than throwing some tools in the back of a wagon,hooking up the oxen,and then camping along the way as you hunt or trap game to eat.
Like it or not,but it took governments to even get this ball rolling,and it will take governments to establish space colonies. Anybody who crosses their screens with "rugged individualist" as a character trait ain't going. ONLY team players get the ride.
Has to be that way.
A lone wagon was a great way to enter the rosters of the dead and disappeared along the trail. Not only were the folks jumping off at St. Joe entering an alien world with challenges different from the one they were leaving, they were often not equipped nor prepared to deal with it either. Trail sides were littered with cast off stuff and the graves of the dead. They moved in groups, as a rule, for safety from hostiles, but the security of being able to pool resources and capitalize on the knowledge of leaders, but even that came mostly later.
The loners moved in small groups of convenience and necessity as well. Only a few moved as individuals.
The resources needed to get there now (space) are as huge and uncommon as were Conestoga wagons in 1820. With time, that will change. There will be an era of the Model T as spaceships go.
As with aviation, when the war (WWI) was over, the surplus planes were cheap, the rules few, and the intrepid with some resources most likely to succeed. The same will happen with space, and equipment out there. It will take much more, but as we expand that sense of freedom will return with a group who just see the challenges of space as everyday things. They will learn orbital mechanics and astrogation at their granny's knee, and with some losses, will step out and explore on their own, not necessarily as individuals, but as smaller and primarily commercial concerns, independent of a central government as they can be. So were the fur traders, prospectors, and eventually settlers (game changer, because they
are civilization, complete with its rules) who follow. (Air and fuel, delta V will just be added to the list of necessities with food and water and shelter from the outside elements (radiation) and electrical power.)
Don't think for a second, that as with those earlier explorers, the government won't follow, fastest where the lucrative resources are.
It is human nature to want to reap the benefits of your risks and not send the bulk of that off to some bureaucrat in a far more secure and, by your local standards, luxurious location.
Without that individual/small group initiative, that expansion will be far slower, and the 'big boys' will be hot on its heels.