New Roles Logic

1.3.88 roles list https://www.screencast.com/t/zByG1w22ezj.

Every user at site with 1.3.88 logic had WP role + UM role https://www.screencast.com/t/T2B2D8K5S8d.
There are many fields (select, multiselect or checkboxes) https://www.screencast.com/t/F5lQ8WFYS80 with selected UM roles. Very important to check this fields after upgrade so they save this previous values. (maybe there will be the list of this fields, because there are many places with such fields).
Since 2.0 you can edit each role at your site and add UM metadata and capabilities https://www.screencast.com/t/pyOKCWQIVjx .  Also you can edit WP Capabilities for each custom UM role, will be provided the list with all WP Capabilities at your site on Add/Edit User Role forms https://www.screencast.com/t/EED18WPlP
The feature for sync UM role with WP role is deprecated in 2.0 version https://www.screencast.com/t/ko6dzWI2.
Since 2.0 all custom UM roles are WP roles and customer can select this roles for every user at it’s sites https://www.screencast.com/t/dfwpApNtYl You can see “Admin” and “TestRole” custom added by UM roles at screenshot.
Also if you selected for user the role, which wasn’t created by UM (default WP roles or roles created by another plugins) you can select second role only from roles created by UM https://www.screencast.com/t/Hn5DnkOC2X https://www.screencast.com/t/DDR8iDvt13c7
this feature is created only for backward compatibility with 1.3.88 version, so we don’t recommend to use it, but you can use it as one of the features if it’s compatible with your logic.
As for upgrade process 1.3.88->2.0 and roles. There are some cases with roles and upgrade logic to 2.0.
1) if UM role has the same name as WP role or another roles already registered at your site. In this case this role will be added to all users, which have Community Role (e.g. Subscriber). All UM settings (role metadata) will be transferred to WP Role
2) if UM role has unique name. In this case this role will be added to WP roles list. Also this role will be added to all users, which have Community Role (e.g. UM Member). UM role metadata leave for this role the same as in 1.3.88
So after upgrade you will see this results for user roles https://www.screencast.com/t/Pe5VVDaS
1) In case if user had WP role “Subscriber” and his Community role was “Subscriber” too – this user will have only “Subscriber” role.
2) In case if user had WP role “Subscriber” and Community role “Member” – this user will have 2 roles after upgrade “Subscriber, Member” !!!Important in this case we recommend to select only one WP role
3) In case if user had WP role “Editor” and Community role “Subscriber” – this user will have 2 roles after upgrade “Subscriber, Editor” !!!Important in this case we recommend to select only one WP role