struggling to grow out and need help with bleaching

hiMy first major problem is that i cut my hair really short in Jan 99 and have been struggling to grow it out since then. I have been trimming it every month and at the moment it just abouit touches my ears in a kinda wannabe bob / mushroom/undercut. It is unlayered in the front withlots of layers at the sides and less layering at the back . My problem is that it is thick and wavy. When it normally reaches it's current length it stops growing and just gets thicker. Also the layers at the sides have started curling and flicking ( a la Farrah Fawcett circa 1977 ) I normally blow it out daily but it has begun to feel like straw so all i have been doing is wetting and gelling it . So far it looks ok.My friends are nagging me to cut and spike it but i don't want to seeing as i used to spike years ago when i was going thriugh my macgyver/Billy Ray Cyrus phase. (ie Short and spiky on top. Long tail at the back ) And looking back i see that spikes don't suit memy other problem is that i am considering going blonde.My naturel colour is a very dark reddish brown. At the moment i am wearing L'Oreals Recital Preference Purple Black in their "Les Noirs Richesse" range. It has started to grow out and my roots are showing reals bad.I want to know if blonde will suit my olive skin tone and also how i can bleach my hair at home.Please help me