Definitely listen to Ray Brown and Charles Mingus. There is also a really good book written by John Goldsby called "The Jazz Bass Book." This book has a foreword by Ron Carter and it basically tells you the history of Jazz Bass. Highly recomended.
Single cuts don't look pretentious. It's just a different form of artistry and design. I like that there is more to choose from in the look of an instrument rather than less to choose from.
I have 3 basses at the moment and have a sentimental attachment to two of them.
One of them I have owned for 23 years and there is no way I will part with it as it was a gift from my parents.