The further you get into the process, the more important it is to hire an attorney.
At the early stages of the initial application and the Reconsideration process, an attorney can help you understand what evidence you have and what evidence you will need to give you the best chance at winning. Getting on the right path early on can make a huge difference.
If you do not have an attorney by the time you request a Hearing before an Administrative Law Judge, you should get one immediately. Do NOT wait until you have a court date. If you wait until you have a court date, the attorney will probably not have enough time to properly prepare your case.
There is no legal requirement that you have an attorney if you are going to court, but keep in mind that even an attorney will hire an attorney before showing up in court.
Hiring an attorney is an easy decision. In most cases, Woodruff and Mathis will only charge a fee if you win.