Update on the gearing, and new chain; so far, so good after several longer rides! Shifting is smooth and reliable, though the transitions between the last 3 largest cogs is a bit rougher as there are bigger tooth count jumps to get up to the 50t cog. No visible chain damage.
I rode out to the steepest grade I know of (that isn't a crazy MTB trail) to test the new granny gear.
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The County Public Works Dept has this road section signed with a grade of 31% at the top and bottom as a warning to trucks. I can't confirm the grade on our USGS topo maps, but they have a minimum contour interval of 40 feet so they leave a lot to the imagination. My take off these maps is that the max grade is more like 22%, but all I really cared about is a test for the new granny gear. It worked great, shifted into the largest cog smoothly. Didn't need to stand to get to the top, unlike last Spring when I rode this with my 11-42t cassette. This gearing change will do the job for me, i.e. guaranteeing I can get home regardless of how tired I am!
Got home with 27% battery remaining after 26+ miles and 2,600 of climbing on a beautiful fall day.