Oh I completely agree a tubeless is easier. With the right technique even the rear of an 800 GS comes off with 6inch tyre levers. Problem for most folk is they don't practice when it doesn't matter, so screw it up when it does. Have a go when it's a sunny day and there's a beer to hand...
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I've always changed my own tyers. I had a f800gsa and did 60,000 km on it in two years. I did at least 4 tyer changes on it + a bit of messing around trying to make it tubeless. I don't know how I'd break down the tyre never mind pop it off the rim. I have to say you are a better man than me to be able to accomplish that task from start to finish in the time frame you have outlined. JJH
