Yeah, I felt bad the other day when I was visiting a boosting farm and reflexively harvested a crop without first checking to see if it was the right season to replant it (it wasn't). Argh. After that I decided to stick to harvesting the trees and flowers (of which there are a lot since it's a dedicated boosting farm).
A few days ago someone mentioned that they like it when people label their fields with signs indicating what they'd like planted there (you can place more than one sign to indicate a choice). Of course, the signs might not make any difference to the kind of people who habitually don't replant. But if someone who likes to plant comes along and sees your sign, they'll know what to do.