Yes, cup and cone bearings (with their angular contact) are more forgiving of alignment. The best example of this is with older English made Raleighs. Many were sold with a low cost headset which had very nearly non angular bearing contact (so the upper and lower races contacted the balls almost exactly in line with the steerer). We had a lot of bikes with headsets that would be loose at one rotational position and tight 90* different rotational position. We faced MANY head tubes and crown seats to correct this. At one point (when the Asian bike parts became so common) we started to just swap out the headset with a low cost angular contact one this took only a bit less time and the nice cutting tools got less chance to be damaged by a mechanic, and the replacement headsets only cost a few dollars.

I ride a CoMotion Speedster with my wife. Maybe I've met your bros? I have to admit that I would find riding the entire Erie Canal path a bit boring...

Yes, I've been building since 1978. Did a couple of short term pro gigs. Now only for me and the wife.

I would hope, as has been mentioned, that a quality frame like a CoMotion would have been fully prepped before shipping. So only minimal paint removal would be needed. Andy.