There's ways of protesting and making points. Protests are a dime a dozen and mostly lead by people that have no idea how resonate with their target audience. If you don't care how your message is perceived, then why should they?
Now I get it. I went back and read your "story." You are young, with a college education, and are adept at using a computer. I really must point out, however, that your narrative had several grammatical errors. If you are planning on using any computer programs to help JWs out of the organization, please be aware of this and perform thorough spell and grammar checks before you publish any information. I can tell you that many people are very put off by reading information that hasn't been correctly spelled or uses poor grammar, so if you want to "resonate with your audience" and "care how your message is perceived" then please be aware of this.
It might help you to know that a large segment of the population is still not completely computer savvy, including, of course, JWs. Obviously, this may not apply to all younger ones, but as a whole, it does. Take me, for example. I am 59 years old, and so know more people in my age bracket and older, many of whom are computer illiterate, or know only how to navigate their e-mail or facebook accounts. Therefore, to grab their attention, protests with placards are sometimes effective. Not all should be assumed to be "people that have no idea now to resonate with their target audience" as evidenced by the current picketing going on in Austin, Texas, by teachers seeking more money for education. They know their target audience, and are reaching them. They've garnered a lot of press coverage, much of it on the front covers of newspapers, and have been featured on television.
As to the dress, I'd like to point out that even Presidential candidates will take off their coats to be perceived as "the common man" while seeking to identify with people, so it doesnt' necessarily follow that all the folks will only take someone seriously if they look like an investment banker. Grooming is important, but the latest style may not be. Rick appears to fall somewhere in the middle-certainly the peer of the majority.
It follows, then, that you might look to technology to help JWs out of the organization, and so does Rick, but your styles would differ, as evidenced by Rick, who also feels that placards and protests still work. Rick may be "resonating with his target audience" by leading protests and attempting to make person to person contact, which is the way we older folk sometimes like to do...that is, engage in conversations with real live people, instead of always communicating through an impersonal computer message. Both can be effective; they are just different modes of reaching people. I think this is his "way of protesting and making points."
Hope this helps you to see that there is room for both avenues of contact with that "target audience."