Homesteaders were somewhat successful, but not as successful as we tend to think they were. We tend to think that the homesteaders were able to succeed easily because they got essentially free land in places that are now (in many cases) very good for agriculture. Some homesteaders did thrive because of these advantages.
However, it was also very difficult for homesteaders to succeed. The land was much less easily farmed in those days before mechanization and irrigation and pesticides. Conditions were harsh in areas with very cold winters and no trees for making houses. These sorts of difficulties made it much harder for homesteaders to succeed.
Historians today argue that much of the success of the homesteaders is overstated and that it was really the big companies with their "bonanza farms" that benefited the most from the opening of the Great Plains.