I’d say when the string no longer seems to hold tension and just doesn’t “react” like a new string. I replace them when they get too frayed for my liking. I live on a farm so my strings tend to get dirty kind of quick. Once the string looks and feels bad, I replace it. They are cheap enough that I never have to truly wear them entirely out.
Think of car tires. You are supposed to replace then once they get down to the wear bars, but they still last longer. I choose to replace tires when I’m within like 1/16th of an inch to the wear bars. I guess I’m the same with strings; they have some life left, but is it really worth malfunction?
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I’m in the “strings are ridiculously cheap so replace them frequently and often” camp.
I mean consider what other consumables are there in this hobby? Silicone response pads? Those last for an insanely long time… Bearings? What is there? It’s just strings, and they’re cheap!
(Even if they’re not cheap, trying fancy strings is also fun and contributes a lot to the overall feeling of yo-yoing. Just ask @edhaponik who won’t use anything but cotton now…)
Also I really like the feel of a new string, it’s like putting on warm underpants fresh outta the dryer… ahh 
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When is it REALLY time for a new string?
If you have to ask a question, you should spend more time playing in less time thinking about it. You’ll know when you know.
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Right. I was thinking about the tire analogy when I wrote the thread. I just feel like Im being wasteful and bourgeois replacing strings like I do. However, I play. A lot.
Yeah, well, Im like rubber and you’re like glue 
Hahaha, I was trying to get all grasshopper on you
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Ahhhh, Kemosabe try teach Tanto. Tanto now wiser 
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I agree wholeheartedly with this @codinghorror. That’s what I meant by feeling bourgeois; I ain’t got that gwop like Big Daddy Code 
I know what you mean, sometimes I feel like that when I take out a string that still holds tension but is just a little too frayed for my liking because I had to undo a couple knots. I try not to let it bother me though, string is cheap enough.
As for the nylon suggestion, yea they last longer, but the feel is entirely different. I love using nylon to change things up (I have like 3 or 4 yoyos set up with nylon), but my heart tells me that I normally want the feel of a standard poly string.
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I can’t agree with this enough. The temptation for a new string is hard to resist sometimes. I will occasionally look through my collection to pick a yoyo to throw for the day and pick the one with the freshest string, or one that needs replacing just so I can get the fresh string feels.
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But bulk strings are like 10 cents each… is it really “bourgeois” to spend 10 cents a day on average, if even that?
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Of course not. That’s called being facetious.