Hey Chris,
We cover how to get changed custom license fields here: https://wyday.com/limelm/help/license-features/#change
For offline activations they need to generate a new activation request and get a new activation response from you. The activation response contains the latest custom license fields, etc.
Basically do what the article says, and if you get TA_E_INET, then give the user the option to do things offline.
RE question #2:
To convert and online activation to an offline activation simply generate an activation request and then send them and activation response. No need to deactivate first.
>> We've also learned that the customer in #2 wants to run multiple users on the same machine, logged in at the same time. We license per user, but were having trouble with the two applications getting the license info of the other - are we doing something wrong?
Yes, activations are node-locked, thus per machine. Even if you use TA_USER theres no guarantee that TA_USER will be used. If you ever use TA_SYSTEM then it will always be converted to using TA_SYSTEM. This is by design.
To do per-user-session licensing use floating licensing: https://wyday.com/limelm/help/licensing-types/#floating