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Double Bass Transitioning...

So, I've been playing bass guitar for 50 years, and recently got it in my head that I should learn to play upright (mostly because of a growing interest in prewar blues, trad jazz, and swing). Are there any others who have done that who have tips? I've always preferred short-scale basses, and the idea of a 40" scale is kind of daunting (though I know the technique is so different that there's no direct comparison). Anyway, what should I be thinking as I shop for a (cheap) upright and what are the stupid mistakes I should try to avoid as I fumble with a new instrument?
 
1st things first GET A TEACHER. You will hurt yourself if you don't have a teacher. That is super important.

2nd there are 3 ways you can go: Get a good plywood near you and learn on that. No issue with that. You can get one for $1000-$2500. If you're able to afford $2500 I highly recommend getting a new upton bass, but you don't need to go that way.

Where in the country are you located if you don't mind me asking?
 
1st things first GET A TEACHER. You will hurt yourself if you don't have a teacher. That is super important.

2nd there are 3 ways you can go: Get a good plywood near you and learn on that

What Sam said--get a teacher, and start on a plywood. Best case, you can find a reputable shop/luthier nearby that will be able to inspect or recommend a plywood starter bass.

Only other bit of wisdom: don't be afraid to start out with lighter strings (Piastro Evah Pirazzi Weichs, or TI Spirocore Weichs). I played my first three years on Mittels (on a poorly setup bass) and almost put myself in the hospital. At our (your) age, don't be a hero. Rock the weichs while you learn the ropes.

(And don't worry about the scale difference. It's a totally different animal.)
 
I think it's important not to get the cart before the horse. The purchase of an instrument should be low on your priority list as a beginner. Instead, I would recommend that you rent and take lessons for some time before you start shopping.

With EB, or guitar, or many other instruments, it's not that hard to evaluate instruments when you can hardly play; there are a lot of reasonable quality reasonably priced instruments out there; and the entry cost is low. On DB, however, all of these are different. The high percentage of hard-to-play self-destructing bass-shaped objects and the high prices of decent instruments, mean you're better off, in my opinion, renting for a while.

I was recently able to pick up a good Squier Precision Bass for $100. I don't really play electric, but I could see that nothing was broken, the pickup sounded good, the neck wasn't twisted, neck relief wasn't excessive, etc. An equivalent "cheap and cheerful, nothing fancy but completely serviceable" double bass probably can't be had for much under $1000 and it is very difficult for a novice to distinguish the cheap and cheerful $1000 bass that will give excellent service from the population of $1000 basses that are either beat to death or of abysmally poor quality or will need another $1000 to make them playable.