Having just come back from a month long trip on an classic bike where film and stills were high on my agenda, let me tell you how it went: badly is the one word summary.
Reflecting on it, a few reasons come to mind. Firstly I was travelling with someone else (on an identical bike as it happens), and recording stuff wasn't as high on their priority list as it was on mine. So inevitably that led to stuff I wanted to do being skipped.
Secondly, it's hard to ride and film at the same time if you're riding solo. I had two GoPros mounted on the bike and even with a remote to control them it's an awkward process. So road safety (inevitably) comes first and often opportunities were missed or took second place to survival. Going back to reride the same stretch of road but this time with the camera turned on mostly fell foul of point one.
Thirdly, equipment reliability. One of my GoPros developed a fault during the trip. It would record video fine when it was hand held and off the bike but with the engine running - ie on the road - it came up with an error message time and time again. Stills were recorded ok but not video. My guess was that it was the high frequency vibration from the engine at the root of it but there was not much to be done on the road other than try to work round it.
Fourthly - time schedules, even unofficial ones ('we ought to make it to X today') play havoc with trying to record your progress. If producing video was a major priority I could see 100 miles a day being about as much as you could accomplish. If you have a limited amount of time for the trip then making progress vs recording progress becomes a serious issue.
And all that is without working out why you're doing - having a 'game plan' and an end goal for the footage. The more I try to do this the more admiration I have for people who seem to do it well. I've yet to go through my raw footage and maybe the secret is all in the editing. I'll see over the next few weeks when I look through it all. Perhaps 'if you can't make it, fake it' is the approach to take. It is make-believe after all.
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