Actually, that's probably the easiest way to do it. If you are collecting and storing the manager in a user custom field, you simply add the field to the notification scheme and they'll start getting the mail (you can send to people like reporter, assignee, group, etc - look for "custom field" on that list)
Sorry for not being clear in the last post.
For each user there will three managers (Resource managers, Work Manager and Business Leader). Depending on the status, the issue has to be assigned to either resource manager or work manager or business leader of the user (User mentioned here can be either reporter or assignee).
Ex. During a "escalate" transition, we would like to assign an issue to work manager (from stored information) of the user.
It depends on your requirements. If they're tied to users, you probably want to do something with your user directories. If they're tied to projects, think about project fields (done by a plugin) or metadata. If they're tied to issues, then your current "log user at the time of issue create/edit" is the right approach.
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