If you are playing a tune in F# major, and at some point the tune modulates to the dominant (a very common modulation), you will be in C# major (not Db major). This is so because you modulate by sharping one single note: B ---> B#.
But if are playing a tune in Ab major, wich at some point modulates to the subdominant (another very common modulation), you will be Db major (not C# major). You modulate by flatting one single note: G ---> Gb.
Of course, if you are playing a piece that is entirely in Db major, you can equally write it the enharmonic key of C#: it is the same piece. That is why Bach has 24 preludes and fugues in each of the 2 books of the WTC (not 30). Same for Chopin's 24 preludes which cover all 24 tonalities. It is actually the point of equal temperament that Bach wanted to demonstrate with WTC: in equal temperament, C# and Db sound exactly the same, i.e. they are enharmonic. With non equal temperament, C# major and Db major would not sound the same, and it would not be possible to go smoothly around the circle of 5ths, so that modulations would be awkward or impossible.
In the WTC, one may wonder why Bach choses to write in C# major (7 sharps) instead of the simpler Db major (only 5 flats). I suspect it is because he uses the same key for both major and minor. Since there is a key of C# minor (4 sharps) and no key of Db minor (that would require double flats in the key signature), he writes in C# rather than Db major.
Wictor Wooten knows all of this, and his point is that one needs to be equally fluent with C# major and Db major, because there are contexts where they are not harmonically equivalent.