[matsemann]

I've had the same problems. Planned bike rides, and often ending up in too rough terrain where I have to push or even carry my bike as it was suddenly a trail and not gravel road.

To help that, I've actually started contributing to Street View. Mounted a 360 cam high over my helmet when I bike, and then use that photo to upload to Mapillary (CC license) and Google.

One is allowed to replace the bottom with a logo ("nadir cap") to hide myself, and because of that I often get people reaching out telling me how useful to check conditions. Not just hardcore bikers, but lots of people just wondering if they can bring their stroller or an elderly family member on some forest walk.

My tooling is here if anyone's interested https://github.com/Matsemann/matsemanns-streetview-tools/

Of course, when I encounter errors I also want to fix that in Open Street Map so that it propagates to other tools. But most casual people aren't using advanced tools to plan their small trip, so having imagery is useful I believe.