Which do you prefer in a jazz group? I prefer an upright bass for most stuff, but some songs (i.e. Channel One Suite by Buddy Rich) just wouldn't sound good with an upright.
I prefer the sound of an upright bass.
i play in my school's jazz band, and i have no formal music education when it comes to the bass. (i play saxophone) so i play my fretless frankenbass i made out of an old Peavey Milestone. it has some Flatwound strings on it, and i love the sound of it.

I am looking to try out an upright bass though, i believe i could do it, now that i have electric bass down pretty good.
I actually started out on upright. I'm playing electric in the marching band this year.
The upright bass has this distinctive sound, very warm and deep, i love it! I would love to try it, although i think after a while i would miss the electric and get bored of the upright, but that's just me.

But as an electric bass player, will I be able to learn to play the upright fast?
The upright would probably be much easier due to the fact that you'll already have all the finger strength + dexterity required, but I'm not sure how much of an advantage you'll have actually learning the instrument. I know that I've tried playing my dad's upright before, expecting it to be like a normal bass, but the strings were tuned differently which made things a little weird. I'm not sure if it's standard to use a different tuning for upright basses or not, but once that hurdle is passed it's as easy as remembering all the fingerings since there are no frets.

tl;dr - yes it should be a little easier, but probably similar to the transition between a fretted and fretless bass.
Alright then, i'll give it a try! I am not sure about this, but from what I know, they are tuned just like the electric although I've seen a lot of 5 strings uprights so with the low B i guess.

Yeah well, I was thinking of trying out the fretless first, thanks for your answer!
It's the same tuning: E-A-D-G

The main difference is the scale length and using only your index, middle, and pinky fingers.