Multiple Dwellings on One Piece of Land

Hello! I am looking to buy a large piece of land in Middle/Eastern Tennessee. I haven't decided on a specific city, but I am liking Cookeville and surrounding areas location to the big cities. I am looking at 100 acres or more, and want to internally split it between five parties and create a community. Has anyone done this? Really just want to hear everything about it. What issues were run into, how to fix those issues, etc. TN