I think I'm following -
basically assigning two instructors and want a look up field for the emails both instructors in a two separate field?
- since its only 2 you could, set the look up to limit # of items shown (one first item, the other last item shown) but you want to ensure you place them in the correct order each time you needed to link them

- i've faced similar challenges when assigning primary / secondary contacts to certain events. Tagging each of them on their linked record doesn't quite work because its varies (they may have more than 1 events but may want to delegate responsibilities to another primary contact) . To make it streamlined from the team we decided to just implement 2 fields linked to contact records for this purpose.
I think I'm following -
basically assigning two instructors and want a look up field for the emails both instructors in a two separate field?
- since its only 2 you could, set the look up to limit # of items shown (one first item, the other last item shown) but you want to ensure you place them in the correct order each time you needed to link them

- i've faced similar challenges when assigning primary / secondary contacts to certain events. Tagging each of them on their linked record doesn't quite work because its varies (they may have more than 1 events but may want to delegate responsibilities to another primary contact) . To make it streamlined from the team we decided to just implement 2 fields linked to contact records for this purpose.
This could work, yes. Hum.
For this instance I think it would work, but wondering if there's an automation that might be able to look in a linked record field, and extrapolate said data in field, and place them, either:
---1) a single field, separated by commas
--2) designated fields for each. Of course, those fields would have to be created so that it could place each, so the number of entries would have to always be the same, as AT wouldn't create fields(that's not very efficient for this task).
This could work, yes. Hum.
For this instance I think it would work, but wondering if there's an automation that might be able to look in a linked record field, and extrapolate said data in field, and place them, either:
---1) a single field, separated by commas
--2) designated fields for each. Of course, those fields would have to be created so that it could place each, so the number of entries would have to always be the same, as AT wouldn't create fields(that's not very efficient for this task).
Yes there is ! If I'm understanding your objective correctly you should be able to place a 'find records' action in the middle of the your trigger and end action

Hope this helps!
Another type of solution


First is good, second needs to remove comma.
Added brackets to clarify a part that must be shown .
REGEX_EXTRACT({field with Emails},',(.*$)')
Also, added 'emptiness check' to fix #ERRORs
IF({field with Emails},
REGEX_EXTRACT({field with Emails},'^[^,]+')
)
it's not enough for second, we need to check for comma:
IF(FIND(',',{field with Emails}),
REGEX_EXTRACT({field with Emails},',(.*$)')
)
Now it's OK
