I don't believe it matters. I just tore down and fully cleaned 3 vertical motors (2 from my FM Trainmaster and 1 from my Alco). In each case I closely observed the orientation of the thrust washers and no two motors were the same. That is no guarantee they were that way from original manufacture, since I bought them used 25 years ago.
But after reassembly, I decided to focus the "flat" sides toward the bushing. Been running them for weeks with no issue - but I would love some old timers to chime in and confirm.
Thanks everyone. Found a Lionel 1955 "Streak Liner Set" November 14, 2020 from the Original owner in a local newspaper listing. Out west, we don't see these very often ( 2 in 50 years of collecting). Pics enclosed for everyone's enjoyment.
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