I've also spent a fair bit of time listening to his lectures and reading his articles, and likewise have (at least usually!) used the terms GNU/Linux and "free software" the way he recommends, because I see where he's coming from and tend to agree.
Does he need clever marketing? I don't know; he didn't for me. What's different about the way I see things?
I think he probably has some personal moral code that prohibits him from trying to hack systems above a certain level of abstraction. Computers and security policies are below it, people's minds, emotions, and opinions are out of reach. In other words, the art of marketing is completely outside it.
YC on the other hand has a much higher bar for what is hackable, including things like getting user growth through clever marketing and viral loops, and keeping your startup solvent by selling breakfast cereal. RMS wouldn't go near these types of things, but they are in line with the hacking ethos.
I think he chooses not to change his way of presenting it because he's presenting a philosophy, rather than simply trying to convince people to agree with him. I used to think he was a nut, the more time that passes, the more I realize just how perceptive and correct RMS has been about a great many things...
The truth is 'hack' as a phrase is becoming overly used, and taking value away from the actual terminology he is trying to advocate, a terminology that is associated to cleverness.
Not everything can be clever. At some point the usage of the phrase turns into marketing hype as a way for someone to gain the attention of a particuliar group.
"A xxx for hackers' "how I hacked xxx"
It's really just a way to grab people who self identify with that word, they don't really mean those pitch lines. It's not FOR hackers, it's TARGETTED at "hackers".
Not every single accomplishment of rms' is a hack. That ambiguity is exactly what is killing the value of that word. Not every action of a hacker is a hack, nor are all the solutions they seek 'hacks.'.
I guess this doesn't quite qualify and he may not even be the originator of the idea, but I thought it was pretty clever:
http://www.wired.com/opinion/2012/11/richard-stallman-softwa...
Feels kind of evil and orwellian. rms (without the premeditated scheming) does something similar but blunt and people resist. We intuitively feel that if you make us use your words, you get power over us.
If the intended audience for his philosophies were only some especially elite group of hackers, that'd be fine (although it'd still be a pretty hard sell for a lot of them :), but I think he sees his intended audience as being all of humanity. When he talks about why Free Software matters, he might be more convincing if he spent more time talking about why openness matters, or even why software matters period. I have a feeling he's so deep into his world that he actually can't see things from the perspective of someone who doesn't understand why software itself is an important thing (never mind how it should be written or distributed).
Tangent: I agree with a lot of the principles that he stands for, but have a hard time trusting his thought processes. Whenever I've read his writings about the origins of his philosophy or the justifications for it, it always seemed like he decided up front what he wanted his philosophy to be, then retconned a bunch of really detailed and articulate rationalizations for it. I don't get the impression that he burns any cycles trying to understand other people's perspectives or playing Devil's Advocate against himself. That's why whenever anyone talks about his consistency as being a virtue (and they always do), it actually makes me trust his reasoning even less.
As a counter, I would say it is sometimes important to fully define something before you seek to implement it - particularly if that thing is subtle or complex or difficult to grasp. And often the person who defines something is a different person to the one who finds a way to implement it. I for one, like the rs' of the world.
Plus, I like to think perhaps there was some subtlety to his point about playfulness.. and maybe one who hacks for a living is just a hack.
Another, possibly more so, is Simon Phipps of the OSI.