What is the biggest bang for your buck thing you need to do everyday to get to the first checkpoint?
Starting doing number 4 everyday without fail. Only focus on number 4. Numbers 1-3 rarely need to be thought about.
Once number 4 is a habit, start slowly adding in more things you can do everyday that will help you get to the next checkpoint.
Adjust and adapt as needed! Focusing on the daily process goals are the real key to goal setting, not the outcome goals or checkpoints. Re-evaluate and adjust accordingly.