The correct answer is in an early post in this thread:
We choose which enharmonic key to use (b versus # version) based on the fewest number of sharps or flats in the key signature that results from using X named key. At least, that is generally the case, unless there is a special reason not to (which doesn't matter for what we're talking about here).
points of note:
- accidentals are not part of a key signature... sharps and flats are called sharps and flats, they only become accidentals when you have to play a written note that falls outside of the key signature. So if you are in Eb Major, and you want to play an E natural, you have to play an E with the natural sign (the little square thing with a couple stick things LoL... no idea if it's type-able here). That is an accidental, and it only lasts as long as the current measure of music, then is forgotten (on purpose).
- Eb Major has 3 flats.
- D# Major has 5 sharps and 2 DOUBLE sharps. (C## and F##).
Which would you choose to write notation in, discuss with other musicians, and read chords from?
I think it's self explanatory, but we use the key with fewer sharps or flats in it (Remember you can't mix them in a key signature). So Eb Major, in my example, is the best choice.