Forgive the morose tone. But I wonder, is there much sorrow in wisdom?
There can be. It depends on the person and their overall outlook and personality, really.
By an appreciation for the complexities of life's questions, the philosopher must confront difficulty and confusion.
Sorrow is not required in the face of difficulty and confusion.
By coming to realize the relative nature of humanity, the philospher struggles to find clarity in the concepts of right and wrong
Not necessarily. I prefer relativity to objectivity, personally. I don't care much for right and wrong. I never struggled to find clarity in the concepts of right and wrong.
Through grasping, if only for a moment, the realm of possibilites in an unknown-universe, the philosopher's life thus far becomes small
Indeed. This is also not necessarily something one must be sorrowful about. I admit I would enjoy being Supreme Overlord of the Universe but being small is something I can be content with.
By gaining knowledge of the vast damage done to people; past, present and future potential, the philosopher is saddened at humanity's legacy
For a time, I was upset about that.
I got over it.
There's no point in regretting it, it's much more productive to try to better the legacy, even a little.
In grasping the subjective nature of knowledge-gained, the philosopher comes to doubt what he thought he knew - doubts moreso all learned thereafter
Also true, but also not necessarily something one must be sorrowful about.
Upon acknowledging our imperfect state of understanding in the universe, the ground on which the theologan stands suddenly feels less firm
Same as above.
As youthful arrogance is eventually supplanted by the humility only the most-honest philosopher will embrace, social interraction rewards that achievement by relegating him to the back of the room in favor of those with the loudest voice, most boistrous claims and most arrogantly-stated claims.
Again, not necessarily something that must be sorrowful. I myself have never had a problem being "in the back of the room."
After digesting the constituent elements, subjective and otherwise, of the lotus, the philosopher suddenly finds that flower not quite as awe-inspiring. It can never match the 'wonder of the unkown'. Much like the virgin, upon experiencing that which was so oft anticipated; yet now has experienced the thing, the magic is gone.
I don't like the unknown. The known is much better, in my opinion.
Upon urking through the complexities of political structures, interpersonal relationships and sociological phenomena, the philosopher; now imbued with a greater understanding, realizes that not a soul cares to hear it. The personal reward (not the least of which includes the journey itself) remains, yet no capitalization on that knowledge - for others - is to be had.
The personal reward is all I really care about in this case. I'm a curious person, I like knowledge and wisdom.