proxy server locating software

I'm new to anonymous surfing and to mac. I want to be able to do the following:
a) hide my true IP when I use a forum, etc
b) not be detected as a proxy user
c) hide my personal info
d) send sensitive email, containing things such as account numbers, safely

I've been reading up on this, and have found a lot of conflicting data. Questions:
1) Is there a software product available for mac that will find elite proxy servers and do all of the above?
2) Do you have any further recommendations on staying anonymous?

I've always just Googles the word "Proxy" and tons of stuff comes up.