Perhaps you should get a contractor to do the job this year while you learn more about the climate in the area. This will give you time to figure out the questions you need to ask. The only dumb question is one you did not ask. Also there is a large store of knowledge on the forum, so ask away.
What we need to know is: where is your land, BUDGET, crop, list tasks tractor will do, background(city/rural bred, engineer etc), to understand where the holes in your knowledge are.
Good Luck.
PS as your skill increases you always get "mission creep"