Set up your first cleanup
Use the Steam edition for the original game. Try one short area before planning a larger cleanup. Agree on a meeting point and work in adjacent patches so players can see where coverage overlaps.
When to invest in automation
Look for work that keeps repeating after a few manual passes. Automating that task helps more than buying equipment before you know which part of the cleanup slows the group down. Check the store for the currently supported player count.