As much as I love having blonde hair and having to bleach it was a pain in the ass. It depends on your hair and it's tempting to go the cheap route and do it yourself but in the end I have no problems going to a salon and paying to have it done. There is a school salon I go to that does a fantastic job. I've colored and bleached my hair far to much and have ruined it at times and having to cut it and regrow it out is no fun. if you end up doing yourself find a hair place that deals with bleaching and coloring and talk to them.
When reading your about your hair problems, I feel really lucky about my hair. I only bleached my hair at a salon the first time I did it, when I bleached it from black to blonde. The black (dyed) side was always more healthy than the blonde (natural) side, and it even stayed healthy during the bleaching. Still, my hair (i'm bleaching all of it now) is really healthy, considering how I rape it all the time when teasing it.