Most of your debug appears to be Kobo output or something? I don't recognize it, but there sure is a lot of it.
I do notice this:
Code:
READING LIST: Metadata available: {'main': {'device_store_uuid': '97dc9975-085a-4dc5-a7f4-a614689983f3', 'device_name': 'Kobo Aura HD', 'prefix': 'G:/', 'date_last_connected': '2020-10-12T21:48:09.238993+00:00', 'location_code': 'main', 'last_library_uuid': None, 'calibre_version': '5.2.0'}}
READING LIST: Sync Now - force_sync= False
READING LIST: Device found to sync to: Kobo Aura HD 97dc9975-085a-4dc5-a7f4-a614689983f3
READING LIST: Not syncing 'To Read' to device as autosync is false
... twice apparently,
Code:
READING LIST: Metadata available: {'main': {'device_store_uuid': '97dc9975-085a-4dc5-a7f4-a614689983f3', 'device_name': 'Kobo Aura HD', 'prefix': 'G:/', 'date_last_connected': '2020-10-12T21:49:05.276982+00:00', 'location_code': 'main', 'last_library_uuid': 'b96decbc-fcca-470f-b7af-8e1338a26310', 'calibre_version': '5.2.0'}}
READING LIST: Sync Now - force_sync= False
READING LIST: Device found to sync to: Kobo Aura HD 97dc9975-085a-4dc5-a7f4-a614689983f3
READING LIST: Not syncing 'To Read' to device as autosync is false
Notice 'Not syncing 'To Read' to device as autosync is false'. Are you
sure you have 'Sync to this device as soon as it is connected' checked for the list in question?
And later:
Code:
READING LIST: Sync Now - force_sync= True
READING LIST: Device found to sync to: Kobo Aura HD 97dc9975-085a-4dc5-a7f4-a614689983f3
READING LIST: Syncing 1 books in 'To Read' to: 97dc9975-085a-4dc5-a7f4-a614689983f3 (location:None)
Presumably the manual sync, which shows no errors.
Is SmartEject asking you to sync
once, or every time you press it? Because if it only asks once, then ejects the second time you press SmartEject, that's working as designed from SmartEject's POV.
Even if it is asking about Sync every time, if Reading List also shows it thinks there's a need to sync (Sync Now option enabled), that's still not a SmartEject issue; it's a RL issue.
What I am seeing looks like you have a list (perhaps a different list than the one you are concentrating on) that is set to update the device, but has the auto sync on connect flag off.