Once Upon a Time Résumés

This is going to sound whack-a-doodle for many jobseekers, but it is worth mentioning. If you were to sell outdated subscriptions, how well do you think would you succeed? For illustration, let us suppose the subscriptions you’re trying to sell are a year out-of-date. What type of static do you think you might encounter?
         Okay, you think I am pandering to obscurity. After all, who is in the market for outdated publications? Damn few, no doubt. Furthermore, locating a market for your outdated product would be nigh to impossible.
Admittedly, this example qualifies as ridiculous, so let us select something closer to reality. To put things into perspective requires a brief comment: Everyday—as in 360-plus a year—résumés arrive in my inbox. One-hundred percent are from jobseekers requesting assistance.
Three-hundred-sixty does not constitute a staggering amount, but multiple that by 20 years and a sizeable figure pops up. Now we are dealing with thousands, and the jobseekers span from New York to California. Many might just as well be trying to sell expired subscriptions.
From a résumé-writing perspective, marketing once-upon-a-time material amounts to a hard sell. Projecting that fresh, up-to-date, with-it image can pose an even greater challenge, especially when a jobseeker entertains an altered-reality mindset.
Writing résumés is easy: Convincing jobseekers that attempting to market old news poses a far greater challenge. A jobseeker with 20-plus years of experience wants to believe his or her record of accomplishment is of substantive value.
To some extent, it is, but that substantive-value portion has severe limitations. Habitually, you will hear or read that one’s résumé should not exceed a certain length. There is no ironclad rule, but like milk, résumés come with expiration dates, which start to expire after ten years.
Why 10 years, or thereabouts? Why not 15, or perhaps 20?
The issue is the message. Every résumé sends a message—intentional or otherwise. No matter how you assuage that message, one way or another, it gets transmitted. Sometimes the message is blatant, but more often than not, it is implied.
Just this morning, a résumé arrived in my inbox from a referral living in Illinois. Her one-and-a-half page résumé is presented in 10-point type, includes four employers, and stretches back to—hold your breath for this1987. That is 27 years!
Honestly, I tried desperately to be objective. I sincerely wanted to give the jobseeker the benefit of a candid assessment, but my eye fixated on 1987. The expiration date stuck in my head. I literally stopped reading. I had gotten her message.
Surely, that was not the message she intended to transmit, but there it was in bold-type no less. I was annoyed with myself for letting that date-reference influence me. There is small doubt the woman qualifies for being honest-to-a-fault. So I asked myself, ‘Will such honesty enable her to cash in those reward miles on her Visa Card?

If I instantly spotted this message, what are the chances an employer will spot it? Does this qualify as merely a minor oops oversight, or does it fall into the oh-shit category?