[Serious] Generally speaking, is philosophy a worthwhile subject of study?

[Belacqua]

That's an interesting point I've never heard before. But again I'd say the same as above; it's not that I would wish the source material itself to change, just at most my own reading comprehension/parsing abilties. So I can fully accept that 'the medium [can be] the message' or that 'oversimplifying [can be] falsifying', whether that be the dialogues of Plato, or Shakespeare like GN mentioned earlier; something would basically get lost in the translation from original form to simplified/modern (or extracted) form, it would be like lossy compression in computing terms ;-)... or similar to poetry, where the words used are meant to evoke multiple meanings etc, and in their case, probably any change at all would destroy their original meaning.

You bring up a good point here, in emphasizing the language. I'd say that's a large part of doing philosophy -- just getting clear on what the words mean.

For example in translations of Aristotle, they might give you eudaemonia, kalon, and arete in some modern English more-or-less equivalent. But a key thing we learn from him is that our modern view of happiness is just very different from eudaemonia, and using the former word as equivalent to the latter is going to be way misleading. Learning why that is is half the battle in learning what Aristotle has to say. Relying on a translation that hasn't bothered with lengthy explanations of the vocabulary is a waste of time. 

This goes back to what Russell was saying: we think we have an idea of happiness, goodness, etc. But when we read Aristotle we discover that very different concepts and systems are possible. Our eyes are opened to different possible worlds. (Science fiction claims to do this, but almost always the characters in distant galaxies have all the values and concepts of modern Americans, and don't even know that alternatives are possible.)

Just about every philosopher, even modern ones, have to use certain terms in specialized ways. But that's no problem -- it's half the fun. And it's not a problem unique to philosophy, since just about every field needs its special terms.