Result: Issue was on my side in how post was specified. This is NOT a LimeLM bug. Thank you for the hint (spotted the missing "[]" in post string)!
We were passing a python dictionary with key entries containing lists, and python requests.post(data=post_data) was incorrectly formatting this post data causing the key overwrite, so only one element of the list was working. It has nothing to do with custom fields with date type (per subject title). In case anyone hits something similar, here is a PYTHON code snippet of our solution, which pre-filters the dictionary and inserts the missing "[]" for list items, then uses the alternative "params" argument in posting:
import requests
post_data {...} # dictionary
params_str = ''
for key, value in post_data.items():
if type(value) is list:
for item in value:
params_str += key + '[]=' + item + '&'
else:
params_str += key + '=' + str(value) + '&'
req = requests.post(url, params=params_str)