Beginner Gardening: Why does it hate me?, 1 by Chris112

Chris112 wrote:
So I moved into a home almost 2 years ago and have been trying to get it to a point I am happy. I previously had a 1/4 acre that looked great and was super easy to maintain, but now have almost 3 acres that started off in bad shape and I am trying my best to recover. I have aerated, fertilized, reseeded, top dressed and seeded etc.. (not all in that order). I also had some trees cleared out to allow for more light and airflow.

Last year I had grass in areas that was just dirt the year before... but now this spring is just dirt again. Some areas are shaded... others not. What should I be doing differently before throwing money at the issue? It seems like after the winter I have this cycle of top soil/seed etc.. My one issue is I can't water as much as I'd like because of being on a well, but otherwise most of my neighbors lawns are in good shape and also on wells.

Help!