I have a lot of respect for Grumpy's point of view, and we always try to move our customer to a tear off to get the underlayment and ventilation to code. That being said . . .
A few years ago we received calls from a couple of customers who we had installed roofs for 25 years previous, installing new shingles over existing roof shingles. Same customers, same house. The shingles used were a 25 year GAF (if memory serves). We found the shingles to be in pretty good shape for their age. No excess loss of granules, not much curling . . .
The customers commented that in those 25 years they had no service issues, and that we were the contractor of choice to install a new roof.
In my professional experience, a second layer may not be a predictor of shorter shingle life.
In the agricultural community I was raised in, and which my grandfather and father provided roofing services to, it was common to install a 2nd and sometimes a 3rd roof. Of course, much of these type of applications were dairy barns and other agricultural structures, along with the occasional farm house (steep pitch, full 2" x 4"/6" rafters).
Call it backwoods or hack roofing, but fact of the matter is that our family enjoyed a reputation of installing trouble free roofs that went the distance, in a community that was pretty quick to identify substandard workmanship. That referral and word-of-mouth kept us busy was the proof of the quality of service offered.
As a licensed professional, I appreciate my heritage, but have moved to a business model that recognizes better value overall in stripping the roof and building a good roof system that meets code.