1. Do the law schools to which you are applying average multiple LSAT scores?
Because most law schools no longer average multiple LSAT scores for applicants, retaking it is more advantageous than it used to be. The highest LSAT score will be the only score that they consider in forming your "admissions index" (a combination of your LSAT score and Grade Point Average which is unique to each law school).
2. Will retaking it delay the review of your application?
Law schools practice rolling admissions. This means that admissions officers review completed applications upon receiving them. This means that the earlier you submit a completed application, the better. Think about whether or not your LSAT score after retaking it will be high enough to counteract the disadvantage of applying later in the admissions cycle.
3. Did something out of the ordinary happen on test day or the few days beforehand?
If you had to deal with an illness, family/personal issue, test center mishap, or another issue that impacted your performance the first time around, retaking it may be in your best interest.
4. How did your performance on practice exams compare to your actual LSAT score?
Think about your performance on practice exams prior to the original score and your overall level of comfort with standardized tests. If your actual LSAT score was at least a few points lower than your practice exam scores, you have the potential to achieve a score that more accurately reflects your abilities.
5. Do you have enough time to study again?
Getting your brain back into "test mode" will require a significant investment of time and effort. Can you study in the morning or evening during the week? Can you study on the weekend? Make a study schedule for yourself between now and your test date to determine if you'll have the time to adequately prepare.
6. How did you study for it the first time?
Take a look at the materials that you used to study the first time around. If you didn't use books containing real LSAT exams, then this may have caused you to get a lower score than you deserved. If you studied from real LSAT exams, but you didn't do enough of them, or you didn't spend enough time reviewing incorrect answers, then you might not have fully understood why you were getting certain questions wrong.
7. Do you believe that you're capable of a higher LSAT score?
Law school is "kind of a big deal." If you believe that you're capable of a higher score, your investment in studying again and retaking the LSAT will pay off when you gain acceptance to a better school, receive scholarship money, and, ultimately, snag a better job when you graduate.