I believe all of the other posters are correct, you can continue to work for the same organization indefinitely. Also, it is important that you know the difference between an independent contractor and an employee; If you are a small business owner, I would encourage you to check out the IRS site for more information. If you or someone else has been working as an independent contractor for a long time you may be considered by the IRS to be an employee- this can become a tricky situation with certain tax considerations attached.
Forever, as long as he/she meets the IRS requirements for an independent contractor
As long as they want to keep paying for his/her services.There s no kind of limitation. Why should there be?