What is the best way to "eyeball" two points perpendicular to a street if you know you will need to offset from one to the other?
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Assuming you are talking about doing offset maneuvers, I always look for an expansion seam or crosswalk that runs across the road. If nothing like that is available I often wonder if the inaccuracy of eyeballing it is better or worse than the inaccuracy of doing a long diagonal to go around the obstruction, so good question.
When you think about it, the longer the particular offset ride, the less inaccuracy is introduced. Of "course", lots of short offsets tend to lengthen a course, but the only time I have wondered about this when measuring the Baltimore Marathon, where several offsets are necessary. With no police protection in a heavily trafficked setting, what choice do we have? I don't particularly care for riding in the dark. I find it much easier to sight tangents in daylight. And I feel safer riding in daylight.
Same experience night riding. Just set up the spreadsheet with columns for "Ride 3." I ALWAYS miss some stretch badly and have to start over. That includes a couple of "wandering" segments I have ridden in daylight and dark for years.