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

Not all 5s are created equal. The regular spacing between the strings at the bridge is 19mm.
Some 5s have a 16mm spacing which many people find too tight Fenders 4s are 19mm and many 5s are now 18mm, which feels similar enough.
Some Bassists prefer 4s, Victor and Marcus predominantly use 4s, and for slapping, etc, I find a 4 is more suitable in some ways; if you have a Low B, damping becomes more involved.
 
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If you've got the need for a 5er like you mentioned then get going ASAP. I tried one on after about 10 years of playing and found no use for it and couldn't get along with wider neck. It felt so foreign to me by that point that I new I'd never have the desire for one Sooner you get comfortable with it and with the ergonomics the better I'd say. What I did like was how much easier it made walking passages etc to play in E & F. But not having it I guess forced me to learn those keys in the open position better. I think if I had more use for one I'd pick up an inexpensive Sire or something of that nature and have some fun recording at home with it on the more modern sounding tracks I build on my own. Would never play it live though. I'd get kicked out of the band if I showed up with a 5 or 6 string bass. :roflmao: But I can respect that.
 
Immediately. A fiver or sixer has all the strings a four does (well, usually- some folks use a high C on their fivers, but in standard tuning, what I said applies).

Unless you are or plan to be in a band where retro styles are absolutely necessary for visual appeal, like a Stones or Skynrd tribute band, or you happen upon a collector-level bass you just can't pass on, there's no real reason these days to buy a four.

Yes, I have four-stringers. I have three, and parts for about five more. I also own two fivers and two sixers. I wouldn't start with a four today if I were beginning.
 
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I'd say if the economy makes eating more important than owning a premium handcrafted instrument you can't play in public for income, about 3-6 months after that would be a good time to buy.

Wait for Tobia, pedulla, modulus, Ken Smith's, Alembics, zon, etc to stack up everywhere under $2000.
 
Are you already a musician? Do you play other instruments? Do you know how music "works?" Do you know how to create bass lines that groove from just a chord sheet, according to the style the song is supposed to be in?

Your question is like a new driver asking if you shoud get a two door convertible or a four door sedan.
 
It’s not a progression thing, like learn on a four, then progress to a five, then progress to a six. I started on a five because I had reasons that made sense for me and I stuck with fives because they continued to make sense for me.

Play whatever you want to play and play whatever helps you be an effective musician in your setting.
 
ASAP! And get a fretless and an upright too.
I have friends that play them all yet at the same time have favorites.
I play them all yet I love the upright most , gig mostly on the 5 string yet am most proficient on the 4 string.
I rarely play the fretless or 6 string but when I don’t have one , I’m always on the hunt.
 
Whenever you’re ready!

If you want to experience 5 or 6 string, go for it!

More strings, wider necks, may feel at home to you or not.

Oddly enough, the more strings a bass has, there are fewer players.
Therefore, there are more 4 string players than 5 string. Just as there are more for 5 than 6. But that means nothing to you as a player, there’s no rule to follow all the others! :)

Another dimension to adding strings is loosing frets and going fretless...and there’s even less players that play fretless. Not that that matters either! :)

I suggest you take your time to experience as many instruments as you like. Make your choice of what you want to experience. Re-evaluate along your “musical journey”. I recommend trying different scale lengths too if you have the chance.
 
Only after mastering a 4 string, or early so that your fingers get used to stretching the extra distance?

Anytime.
There's no natural progression. People often start on 4 strings because they're more common, although these days 5 string basses are everywhere too, six less so but they aren't rare either.
If you are interested in 5/6 strings, then start as soon as you can.
 
It's not a matter of skill it's a matter of interest. I have been playing for over 20 years and have no interest in playing more than 4 strings, but if you are buying your first bass and do then by all means buy a 5 string and learn to play it.