In Back to the Future Part II, why is old Biff in a lot of pain?

In Back to the Future Part II, there is a scene where old Biff exits the DeLorean. Here he seems to be in a lot of discomfort. He breaks his cane too. He just made himself a rich man, shouldn't he been seen coming back happy?

Answer

Short answer:

He accidentally altered time into a timeline in which he did not exist in 2015.

Longer Answer

Old Biff altered the events of time and as such possibly endangered his own future. As you state, Old Biff makes his earlier self a rich and insanely powerful man, basically owning all of Hill Valley.

In a deleted Scene from the movie, that can be found here, you see that not only is he in a lot pain, but he actually disappears from existence. It is my reasoning that once he landed again in 2015, the changes he made started to solidify and as Marty and Doc enters the DeLorean, the new timeline is completed, thus removing Old Biff from existence.

While the DeLorean was still on the ground, there was a still a chance, however slim, for Old Biff to get back and reverse the ultimately deadly changes he made and as such, he was "only" in pain (similar to what Marty felt when playing at the Enchantment under the Sea dance before his parents kissed), but when the DeLorean took to the air, that chance disappeared and with it, Old Biff.

The official BTTF FAQ, found here, states, admittedly rather jokingly, that Lorraine shot Biff around year 1996 in the new timeline. Whether this exact event actually happened or some other ill fate came over him between 1985 and 2015, we can assume that he no longer existed in the 2015 in the new timeline and thus disappeared from existence.

Gale: Our intention regarding old Biff was that upon his return to 2015, he would be erased from existence because he had changed his entire destiny by giving his younger self the Sports Almanac. (Probably, Lorraine shot him sometime around 1996!)

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