It depends on how light your bleaching it. If your bleaching it to a golden blonde then you should be fine but if your going for a platinum blonde then there is more bleach and chemicals in it and it will damage the hair more. You shouldn't be too worried about your hair getting severely damaged unless your bleaching it over and over and over in one day. I think the best way to get to your desired color is to do it gradually. Get highlights one day and get more a week later. Or color your hair with bleach one day, let your hair relax for a few days then color it again. Something like that. Just remember to deep condition your hair after coloring and that should help. I went to cosmetology school so I have seen some bad hair colors but it's all because people don't know enough about it, so I hope this helps!
My hair is naturally pretty blonde but I have done an 'all over' bleach a few times before and honestly if you take good care of it, do deep treatments, use vitamin sprays or any other silk treatments you will be fine... My advice to you is to go ahead and dye/bleach it but never leave the dye on for longer than the posted time, dont brush your hair terribly hard or fast for the first 5-7 days after bleaching,. my hair is sooooooooooOOOooooOOooo soft and like I said I bleached the living shit out of it. If you want for added shine/softness buy yourself a boar hair brush... :) good luck!
i wouldn't go more than 3 times honestly.. 4 would be the absolute max. im kinda a scaredycat when it comes to bleach. thats a lot of damage on your hair. just be sure to follow up with a deep conditioner lol. but i guess it does depend on your personal hair. if it doesn't appear to be or feel extremely damaged, you could probably go for another 1-2 rounds. good luck
I've bleached only sections of my hair, not my entire head. And not nearly as many times as you have, but my hair is some of the softest hair you'll ever feel. I do know other people who frequently bleach their hair and they still have a lot of it (their hair started out thick to begin with, though) and it's only slightly damaged - a bit on the coarse side, but not untouchable.