No doubt there would be a lot work to do to do a plan like this. You would need to figure out how to put it all together, do all the calculations, do a lot of what if's, etc.. And I'm sure one of the biggest things would be, would you actually take the time to do something like this or even have the time to do it? You could pay someone to do it but that would probably cost you a lot. Plus if you did that, most likely it would require a lot of back and forth work to get it just like you wanted it which would be even more expensive. But even then, would you spend the money to do it? There is a better way. If you would like to develop a nice plan like this for yourself and give yourself a good shot at making your life better, then find a planning software that does it all for you.
The "Accidental Entrepreneur" Plan: Believe it or not, it happens quite often. An impulse, a hobby, or a passing notion turns into a business without warning. One day you're handing your extra back_yard tomatoes or homemade cake to the neighbors, and before you know it you're filling out the forms for a booth at the local farmer's market. Perhaps you create a unique bit of hand_crafted jewelry and wear it to school or work, and then find your phone flooded with messages like, "Where can I get one?" and "I'll pay you to make one for me."