How Far?

   At what point are you no longer helping someone and have started enabling their destructive lifestyle?  Obviously, you want to help people and see that they make strides to get their life on track and in many cases you will do whatever you need to facilitate that. At some point I think you reach a point when the things that you are doing to help that person are no longer helping them, indeed you are doing the exact opposite. Take for example a woman who we will call "Sara" who has not held a job in nearly a year, lives with "James" and pays what amounts to a pittance when she does have money. 

  In exchange for providing Sara with a roof over her head and food to eat and sometimes even childcare of Sara's baby James only asked that Sara clean. James did not think this to be a problem because Sara does not have a job. Yes, Sara would have to clean up after James sometimes in addition to other cleaning but it's only right because James is paying her living bills. James does all of this because he wants to see Sara progress and do something with her life. Partially because James loves Sara and wants to see her do well and partially so Sara can stop mooching off of him. The problem is that Sara hasn't done anything tangible besides talk a good game about doing something with her life. She isn't in school, doesn't seem to be looking for a job. On top of all of that Sara doesn't even clean up after herself properly. 

In this example, when is James doing Sara a disservice by allowing her self destructive lifestyle to continue? At what point does James tell Sara, look you either achieve "x" by "x" date or you have to get out and find your own road? What exactly are James' options here?