I think clarinet to oboe is a probably more of a joy than flute to oboe.
I went from flute to oboe ages ago and even though the fingerings were similar getting the fingers to move at the speed as you are accustomed to the flute (if you play well) can be a chore.
I went back to flute as my primary as I loved the flute more in the end. However I still have oboes and play around with them as sometimes oboe just expresses some things better than flute... like laments and vocal scores.
The flute is especially powerful as a solo instrument for church, weddings, funerals, and New Years. The flute is highly emotional/spiritual and its sound can bring forth a flood of emotion. There's also fun latin/jazz flute stuff.
However in a band/orchestra setting with many flutes the oboe shines for individual expression, especially if you like to be showy. Plenty of good oboe solos abound to make people eat their hearts out. It's those oboe moments of extreme poignancy that is the big thing with the oboe. It is incredibly amazing when you have one of those moments and the world stands still.
But then there's the reeds and the practice.
Ah! An oboe moment, Gabriel's oboe:
http://youtube.com/watch?v=PRb8KKyenSY
Oh! A flute moment, Siesta:
http://youtube.com/watch?v=bKgwQgr8DRc
Flute Pop:
http://www.youtube.com/watch?v=rqTCc5ZOojU
Oboe Jazz:
http://www.youtube.com/watch?v=_TIP8swMSi8
A Quartet (Seasame Street):
http://www.youtube.com/watch?v=1h7HKg8M7xE