I tried to teach myself when i started, destroyed 2 kites and was lucky not to hurt myself or someone else. When i finaly got a lesson i got to work out what i was doing wrong lots of dumb mistakes. They didnt fly the trainer kite for long in the lesson and dont think you really need one of you are doing lessons.
After my lessons i was a much better kiter and was soon ridding comfortably. If i didnt get lessons i think i would have given up.
Get lessons before you buy the gear, you may be a natural and be able to get some gear that will last you. The instructors will give some good advice, so listen to what he suggests.