First, I think it has something to do with her pop culture placement. She began making a name for her self in the midst of two titans; Katy Perry and Lady Gaga. This is a bit like being P!nk when the world was watching Britney Spears and Christina Aguilera, or being The Kinks when the big battle was between The Beatles and The Rolling Stones. There is always a dark horse who gets some attention, but never quite competes. She is the third party candidate in the Presidential election.
Second, is the AutoTune. It is obvious that she is on AutoTune almost full time. This led me to believe that she was all image with good producers. Kind of a Milli Vanilli, if you will.
Third, I was pretty sure I had heard all of this before. Ke$ha's music is kind of about being drunk and slutty. I felt she owed the Millionaires some royalties.
So, I decided to do a little Ke$ha research on the always reliable </sarcasm> Wikipedia. Turns out she plays guitar and piano (how well they did not say), and had songwriting credits prior to releasing her first album; a plus in my book.
As of writing this, I still have not made up my mind. Is she a vapid teenager who can't sing and uses provocative lyrics to get attention? Is she perhaps a semi-ignored talent that someday we will give high praise to? I don't know, but what I will say is that she at least stays on message. Her drinking and sex persona goes through her music, not just that first "notice me" song (looking at you, Katy Perry). Maybe her use of AutoTune is ironic, or merely for effect? Lady Gaga uses it, though it is clear that she does not need to if you have heard her sing live.
So, I am withholding judgment. Her songs are definitely solid dance pop music, which she deserves at least part of the credit for (producers really make the album some times). If she likes the things I like, that is a plus as well. Stay trashy, Ke$ha. We need it in this world.