As you know, octane is how we measure the fuel's resistance to igniting too early--before the spark hits it--causing problems that range from knocking (aka pinging) to burning a hole in the piston to trying to make the engine run backward. So real damage can occur. BUT modern engine control systems (ECM) have knock sensors to detect the problem, and when it happens, the ECM takes steps to reduce it. When it does, you usually are going to have less power available.
If you are in a situation where you need the power, such as passing uphill, and can't afford to roll off or have the engine deliver less power...
Several answers here I agree with but this one I really relate to:
There was a woman in town that bought a new Corvette all most every 18-24 months, which was several years ago. One day I noticed she was parked at the station with the cheapest gas, soon after her first purchase. I had a connection with the Dlrshp that sold the cars. Every Corvette she owned was having engine problems. Usually burning up coils. If I remember correctly 2 ? cyl per coil back then. The ECM as you have figured out, compensated for the crap and that was the result. Are they much different today ? maybe !
Stick the key in and drive, when you have a problem read the owners manual, seems to be the American way.
Wife just got a 2015 VW Golf, manual looks like a cut down phone book, and thinner pages to get it in the glove box. Flashing the ECM will pick up as much as 50% more HP from the 170 out of the box. But you can't guarantee the # of octane you're paying for, so flashing may take a down side.....J