We learn by our mistakes/missteps, you have just added to your knowledge base.
Blimey at this rate we'll all be coming to you on how to fix our bikes.Good for you, you've done more to Barney since you've had had him, than most people I've known do to theirs in years of ownership.
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that was quite an elaborate system, but I admire your initiative
It's very risky to kneel by your bike and try to hold it vertical at the same time. I wouldn't do it.
That's what the lift is for, routine maintenance, etc., as you noted.
I don't rely on low fuel lights, etc., I always set the odometer back to zero at each fill-up and when it reads 125-140 miles (200-225 kilometers up here) I start looking for gas - or sooner if I'm in a remote area.
There are many wheel chocks on the market so it's just a matter of choosing one you like.
I have the Baxley Sport Chock which works very well.
Baxley Trailer Sport Chock