The log suggests that it upgrades, then downgrades:
core-ssh:~# hassio ha logs
2019-11-14 01:55:45 INFO (SyncWorker_3) [homeassistant.config] Upgrading configuration directory from 0.101.3 to 0.82.1
2019-11-14 01:55:45 INFO (SyncWorker_3) [homeassistant.config] Migrating old system configuration files to new locations
That is a huge leap. Pretty much impossible to update directly to that without some sort of issue. You should read through the release notes for each version and run the configuration check add-on to see what it comes up with.
Nearly 20 releases… that’s, not going to be fun. It’s likely you’ve got a stack of breaking changes causing you issues.
If you really want to upgrade, you’ll need to read every breaking change in _every release since 0.82 and ensure you’ve addressed that. Then you upgrade.
Alternatively, disable almost everything (and that particularly includes api_password) - add default_config: (see here) and leave the rest of http, and try the upgrade again.
It may well be quicker to start with a fresh install and rebuild your configuration.
After chatting on Discord, I went ahead and upgraded about 5 revs at a time, running
ha hassio check
after each upgrade, disabling/correcting things after each upgrade. Things mostly worked, gave up on tts for now and still working on getting appdemon to authenticate.