I think if you take some time to look at the fender mount, you will find it is easy to remove. Remove it and take a look at whats left, see what you want it to look like and move from there.
Sounds like you want the "bobber" look and not necessarily exactly true to the original bobbers. I would leave the front brake alone, you can still have a great looking bike with the front brake on. Not sure what model you have, but you can play with removing the front fender and pull the plastic chrome pieces off and metal chrome pieces off, scuff them up paint them color of choice, wrap the exhaust, if it is a stock exhaust take a look at the mods section you can trim it, cut it, remove baffles, drill baffles, what ever then alot of people like the wrapped exhaust look.
I would search some pictures and start saving pictures of pieces you want your bike to look like. ie what bars, what fender, what exhaust, what painted, and what not.
HAVE FUN!!