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At what point should a new player try a 5 or 6 string?

I played a 4 briefly when I started, but switched to a 5 almost immediately. Played one exclusively for 15 years, then tried going back to a 4. Some say a 4 is "easier", but it still required a period of adaptation. I can switch back and forth and play either with no trouble now. Picked up a 6 recently, for the first time after 30 years of playing. Although I can play it fine, I don't enjoy it as much as 4's and 5's.

Bottom line is try different configurations to see what clicks with you. Long scale, short scale, fanned-fret, fretless... You never know when you'll come across something you love. Also, nothing to say your preferences can't change over time, so keep trying different things along the way.
 
There is no set time. You could've started on 5 or 6, and actually I may have been easier in a way because you wouldn't have to get used to a B string which can take a little while to get used to.
If you think you want to play 5 or 6, you can start anytime. Just put your 4 string away for a while and dedicate to learning all the new strings together.
 
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Why not a 3-string cigar-box bass? Great for busking!!
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Only after mastering a 4 string, or early so that your fingers get used to stretching the extra distance?

Do you need a 5 string bass? If you have a requirement then get one. Don't get a 5 string bass if you are just ticking boxes.

There is no extra distance to stretch. If your technique is good then you won't be stretching on any instrument.
 
As a person who played 4,5, and 6 and then went back to 4:

Get a 5 or a 6 when you need it to gig or you feel fully comfortable with the 4 string and you have musically matured and are ready to move on.

I have seen some local folks with sixes that can wiggle their fingers, but are pretty useless when it comes to holding down the bass fort.
 
It’s subjective to the person. It’s like asking how long should I stay on the crapper looking at the internet before deciding to get up only to realize your legs have fallen asleep thus crashing into the tub and striking your melon on the towel bar only to awaken and realize you bought a accordion off of Reverb and somehow joined a death metal polka band touring Southeast Asia.
 
When I started playing bass I went straight to a five-string. No problems and no regrets. (That is, no problems related to number of strings; I'm not claiming to have perfect technique in a general sense.)

When I started I already had a few years of (thin-string) guitar experience, but switching back and forth between five-string bass and six-string guitar doesn't feel confusing because I approach bass and guitar differently.

After more than twenty years playing five-string I finally started playing four-string as well (not instead) last year, and have been enjoying that too, but fivers will always be my preference.
 
I probably would’ve started out on a 5-string, but it was 1991, I was 15, and locally, they only existed in music catalogs from NYC.
When I eventually ended up with one, and I did have the same apprehension, turns out there was nothing mystical or sacred about getting a 5-string, and I never had the feeling of being more of an accomplished Musician for having one.
Like many here say, just another tool.