A possible fix could be changing the iD warning message slightly:

“Possible error - road crosses waterway

DO YOU KNOW WHAT”S THERE? (in Bold!)

If so, please tag as either bridge, tunnel or ford.

If you’re not certain, please “ignore”.

Thanks!”

“even has 2 DWG participants started off as a joke”

Yep, even DWG members are allowed to be normal mappers, & human beings, in their down time, so are allowed to share in “joke” threads!

For your shown example directions, could you please possibly have them from and to the same places, which would let us see differences better?

Re “If a changeset has multiple issues, try to focus on one major issue, rather than itemizing every single problem”.

An easy option there is too add multiple CCs! 1st is you mention “aaa”, 2nd “bbb” & so on.

As everybody has said though, polite, friendly, & helpful are the main things, rather than “You’ve made a mess”! :-(