My hair is naturally blonde , & about 2 years ago I dyed it dark brown . Well recently I've decided to go back to blonde . My roots are bleach blonde , but the rest of my hair is a medium orange . I've bleached my hair multiple times within the month & my hair is starting to break off . Should I dye all my hair a light brown and start over in like 2 months ? HELP !

Depends on the product you use. Covering it up may very well cause your already fragile and damaged hair to be even worse.

Id stay away from the bleach. I wouldn't dye it for a few weeks just to give it a rest from all the dye. Its just going to get worse.
If you want blonde the best thing would be to go to a salon. Ut if not. You should go to the lightest brown possible and then maybe do a lot of highlights every few weeks. And just keel doing them every week or two until you get the blonde you want . Id get one of the bleachblonde highlight kits that come with the caop. Those work good for doing it on your own,