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How do flats die?

I understand rounds (arguably) die when the brightness is gone, typically after a few months of use. But how do flats die as in when or at one point do you know it’s time to change them?
At least when they won't intonate or stay in tune. I have changed flats after a couple of years when they lose definition on the pitches, usually it happens on the E string.
 
At least when they won't intonate or stay in tune. I have changed flats after a couple of years when they lose definition on the pitches, usually it happens on the E string.

Exactly. By uneven strain, the string loses its ability to vibrate evenly, hence the higher harmonics start to mismatch with the basic frequency of the string.

If you start to ask yourself questions like 'I play a single note and it sounds out of tune, have I gone nuts?'
or even 'I play a single note and it sounds out of tune, have I developed absolute pitch?' - the answer is 'No, it's time to change my flats.'
 
They might break but they never die!

I read an article about Keith Ferguson. One day, one of his flat wound strings broke and he freaked out and drove all around Austin, Tx looking for a used flat wound G replacement. He didn't want to replace his old flats with a new set.

Jamerson was another who NEVER replaced his flats! Carol Kaye, 6 and more years per set.

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A luthier friend of mine had a set of Thomastiks that were 12 years old. He changed them when the G string wouldn't hold pitch anymore. I have a set of D'addario slow wounds on a fretless that are at least 17 years old. I change my main fretted every 3 months for that fresh bright tone.
 
On EB, they can be there for a while 10 years maybe for the typical TB weekend warrior, 5 for the pro.

Over on the DB string classifieds, old Thomastik Spirocores are fought over like the last piece of pie. I did not change since I got my upright in 1992 until 2005, And it was already old when I got it. Going to this site now I have bought 8 sets probably but I have now calmed down
 
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Like DB strings, when they really warp and tear apart on the inside, they lose their ability to produce definitive pitch, and start to sound more like a tin drum than a string. It's pretty obvious, and I don't think I've come across it in the wild more than once or twice. If the string has a steel core, that deterioration basically takes a decade of hard playing to happen.

More often, they just gradually lose brightness and responsiveness until the player decides they want to try something new. Then you put the new strings on and you say "hmm, I guess those old strings were getting a little dull after all." On DB, with a bow, it's a little more obvious because a dullish string won't respond to certain techniques, but when you are only thumping with fingers the note is always going to sound as long as the string is physically holding together.
 
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I had a G string with at least ten years on it break at the tuner when I was putting them on my SCPB. I retired the set out of respect. The new ones have started to calm down after about a year, but I don't play that bass as often as I should. My guess is that the new set will live longer than I will, Not sure though, because that particular bass has a white pickguard instead of tortoise, just might change things