You probably don't think much about the words "fewer" and "less" unless you see a sentence that jars or you are trying to decide which to use in a sentence.
I happen to be thinking about them today because I was jarred by a sentence in 
an email.
Some sentences do jar, but leave you going back to see why. The meaning is clear, so?
For example: "The cashier wished less people would complain to her about the grocery prices."
You know exactly what it means, and yet it feels wrong. It should have said "fewer people."
Is there a rule for that? Of course.
The general rule is that fewer is used when the topic can be counted, as in fewer problems, fewer choices, and fewer clouds in the sky.
Less is (always but not only) used when the number is measured, as in less time or less effort. Interestingly, we seldom see anyone get it wrong in this instance. Anyway, I've never heard anyone say fewer time or fewer effort.
Are there exceptions to the rule. Also of course.
We count dollars. But we don't say that a gallon of milk costs fewer than $5. We say less than $5. On the other hand, we might say "I have fewer than 5 dollar bills in my wallet."
Back at the grocery store, the fast checkout lane always says "10 items or less." They never say 10 items or fewer, even though it is probably correct.
I didn't find it written anywhere, but it looks to me that the exception goes into effect when the counting reflects actual numbers.
We would therefore say "Fewer people than expected attended the rally," but then say "Less than 200 people attended the rally."
However, that's not a hard and fast rule either. When you're writing a property description for one of your listings, it could go either way.
You could say "I have to say all this in fewer than 1200 characters."
Or
"I have to say all this in 1200 characters or less."
So it depends on the sentence structure.
Why does this matter?
For the same reason that all grammar issues matter. When a prospect is reading 
your beautiful promotional words and gets stopped mid-sentence, you've lost the flow.
They might have been reading along, nodding their heads in agreement with you, and then all of a sudden, it stops. They may only notice that something is off, so stop to look twice. Or - depending upon the error - they may not understand what you meant. Either way, the magic is over.
My best advice: Follow the rule most of the time, but if it doesn't sound quite right, follow your ears! In other words, be sure you read what you wrote (proofread) before you send it out.
And if you aren't sure - ask someone else to proofread for you!
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