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Hi, LegendTom. I'll throw my two cents and personal experience into the hopper.
First, what I learned in my fuels class: As CT pointed out, octane ratings essentially are anti-knock. Higher the rating, less likely to ignite under compression. High compression engines need higher octane. Using high octane in low compression engine means that fuel won't ignite (plugs foul); using low octane in high compression engine means fuel will ignite too soon (detonation, ping).
Ironically, if you make a habit out of using high octane when you need low octane, you end up causing carbon buildup in cylinders; then, you've effectively reduced combustion chamber, increased your compression ratio, and create an artificial need to keep using higher octane.
That said, I don't think that it's always a "waste of time" or a waste of money to use varying octanes. Modern cars (unsure about Triumph motorcycles) have knock sensors. Depending upon the octane, they help adjust the timing and performance, so that if you use a higher than recommended octane, your performance profile changes without harm to the engine.
As for my Triumph, I also have a Legend. The manual says "minimum" 89 octane. Well, when my bike was new, I tried 89 octane. Bike pinged; performance sucked. I've been using 91 octane ever since and am quite pleased....Jerry
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