We did it for one of our client application. Granted it was done in .NET for Windows, but the same principles can be applied in MAC.
Like eckesickle mentioned, if your user have access to the internet (or should), then you can have a web service that will register some unique id from the host computer with the starting date trial (MAC adress is a good one). With this, the user cannot really cheat the program unless he chances his network card every month.
Now, if the user doesn't have access to the Internet for some reason, you can either shut down the program until he connect to it or use a grace period. This file records the last time the app is opened. When the Internet is not accessible, we stop writing the time (we still write something in it so the user doesn't notice the file is not updated).
Should a user notice that this file contains the information and delete it (or change it using a copy he has), then you need a way to counter that. You can have some other value in another config file (encrypted always) and check for consistency. What you do if you discover that the user is trying to cheat is up to you, but we force the user to connect to the internet for it to work.
It might be overkill for a program, but it definitly works.