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So I use schwalbe one 25C tires and they measure more like 27-28mm when inflated on my rims. I normally use Conti tubes the 28 race. These are for 18-25C. However, should I be using the "wide" version since my actual measurement is more than 25?
 

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No.

No need to take my word for it. Blow up a tube outside a tires and you'll see they get really big. I used 18-23 tubes on 33mm tires not problem.
 

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No.

No need to take my word for it. Blow up a tube outside a tires and you'll see they get really big. I used 18-23 tubes on 33mm tires not problem.
yeah, they certainly go a lot bigger than the tyre they are in. On a related note though, is there any benefit to puncture resistance if you use a bigger tube in a bigger tyre as it isn't stretched as much as a smaller diameter tube?
 

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Many run a 2.4-2.75 tube in a 4" fat bike tire without issue. Being a few mm off on a road bike is not a problem. When stranded on a rural route after a string a flats exhausted our tubes/patches, a rancher provided us with a 650 tube. It stretched on a 700c wheel and worked to get us home.
 

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On a related note though, is there any benefit to puncture resistance if you use a bigger tube in a bigger tyre as it isn't stretched as much as a smaller diameter tube?
If there is a benefit, it hasn't been measured because it's probably too small to notice. By the time a sharp object has made it through the tire the tube is practically helpless.
 

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Yes, since a stretched tube is thinner, the air permeates through the thinner rubber faster. Note: not the classic definition of a leak. How much faster? Hardly any.
OK, good. And, yeah, my choice of words was not the best. Thanks for getting what I meant vs what I said!
 
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