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Moving to upright bass...

It was a LONG time ago, but the first thing to embrace is the GIGO (garbge in, garbage out) philosophy of amplification. If you get a thin, non-projecting sound out of the instrument, when you amplify it you get a LOUDER thin, non-projecting sound. No amount of knob twiddling, string changing, instrument changing is going to get you to a warm, open, projecting sound; THAT you have to be able to physically produce from the instrument itself.
After playing DB for 18 years or so, I finally went to a teacher (about 13 years ago?) that got me to a place in physical approach that I do a majority of my gigs without an amplifier. Playing with a projecting sound isn't about playing harder, it's about playing smarter.
 
I did it for the sake of loving the instrument and also to get more gigs, which it definitely does. Add jazz and bluegrass to rock and you get the calls more often.

The hardest thing, to me, is that your hands do quite different things physically on an upright than on a BG. The left hand especially. I strongly suggest taking at least a few lessons to begin with.
 
If you get a UB before taking lessons, dont play it more than a day or so.

The more you play it (before getting proper instruction), the longer it will take to unlearn all the mistakes you'll make on those first few days.

Keep in mind the only thing a bass guitar has in common with a UB is they both have 4 strings tuned in 4ths. The similarities kinda stop there.

You'll be using your pinky alot.;)
 
Why? Because I'd always wanted to and joining an alt-country band was the kick in the pants I needed to finally get an upright.

The biggest challenge has been, once my hands got strong enough to take on the physical nature of the instrument, intonation. I'm solid to the fifth 'fret', but above that I still have a lot of work to do. Unfortunately, with two bands and a full time job I don't have as much time and energy as I would like to devote to the instrument.