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It's also worth while to google octane and learn just exactly what octane means. Most people are surprised by what they learn.Several threads on this exact topic, search away.
As for cheaper gas (Costco, Sam's club, Bob's Gas 'n Go, etc), I refuse to buy it. I bought some gas from a cheap fill station one time (I think it was giant eagle, but this was 10 years ago so I don't honestly remember), and there was more water in the gas than gas. Never again. Saving a couple bucks per tank just isn't worth it. I know that moisture can find its way into ANY brand of gas, but I've never had an issue with shell, so that's what I'll continue to use.

I find that the ~$10 or so more a tank is easily offset by the ~1mpg better that I get. I run 93 V-Power in all my cars.
EDIT: If your going to run 87-ish. Dont fill it up with junk - go to a top tier distributor. Exxon, Mobil, Shell, Chevron, Turkey Hill etc
One more thing, the $10 difference a tank is nothing when it costs 60-70 to fill up. perhaps a cruiser is not your best bet now.
Your doing it backwards....Add high(est) octane when we go to Lake Tahoe for our winter vacations or going into altitudes but that's it.
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Your doing it backwards.
Higher octane fuel contains combustion inhibitors to prevent pre-ignition (pinging). Pre-ignition is less of a problem at higher altitudes (lower atmospheric pressure).
In reality I should switch to higher octane when we go down to the Bay area from Reno. However I never do and we haven't noticed any problems with pinging.
What is the connection between vehicle load and fuel combustion rate?True if you're staying at altitude, but if you're pulling a load up to the vacation place then higher octane may be a good idea to help with the power/heat of the grade. Similarly, I probably wouldn't want 85 in my tank if I came back down to sea level.
What is the connection between vehicle load and fuel combustion rate?