Latest version of Redirect module failed to run updates.

The most likely problem is that on your second site you had a patch applied that provided an update function with the number 8110, so Drupal didn't run redirect_update_8110() again (the function which adds the 'enabled' field). You can fix this situation quite easily by running this Drush command:

drush php:eval "\Drupal::service('update.update_hook_registry')->setInstalledVersion('redirect', 8109);"

That will make Drupal aware that the last update function that ran for the Redirect module is redirect_update_8109(), so it will correctly pick up and execute redirect_update_8110() when you run the database updates.

In regards to that new feature, I have to say I think that entire feature was done backwards - and counterintuitive to how the module originally handles redirect entries. Should it not have been a "Disabled" field boolean added as the new option instead, this way no existing redirects would need to be updated risking catastrophe and failures? Then it would have been a simple check it to disable it.

This assessment is incorrect, the new enabled field is set to TRUE by default, which means you don't have to update any existing redirects, and there's no behavior change for new ones as well.

Thanks so much @amateescu, this worked for me and I was able to run the update.

@amateescu indeed that worked, thank you.. Tho I still disagree with the manner of implementation. Adding a "Disabled" field and not requiring the update of hundreds if not thousands of redirects (as in my case) would have been the better, safer path.