In the end, for sakura con, i decided to go with a combination of the naruto suggestions and the suggestion of buying a pre-made cosplay from a site that makes them and stocks them, ready to ship out. There is no need to wait for it to be made so all there is to it is the shipping, which can be as fast as 2-3 days with express shipping apparently. Which Naruto character i am going with though, you'll have to wait and see hehe.
Also i noticed that killer Bee had been suggested more than once, but i'll save him for next year. I am a big fan of Killer Bee, but at this time there is no way i could afford his outfit and all the swords on top of that (because God knows i wont be happy with just a couple of his swords).
I am just starting out seeing as this will be my first time actually cosplaying, but thanks to this thread i already have a nice list of potential characters to cosplay in the future, and the best part is that i'll have the necessary time to not rush them