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Can you provide additional information to help clarify your conversion starting point and final end point?
What is your current environment and how are you using MS Project to run projects?
Do you have 3-5 PMs or 300?
Are the PMs using the schedules to capture actual work and if so how?
How large are the schedules in number of tasks, total hours, and total duration?
What version of project?
Are these active projects? Meaning some projects might be just starting, projects are started and have varying degrees of completeness.
Are these completed projects?
Has actual work been applied to these projects either thru manual entry of actual work or thru timesheet entry, or by using task level % complete?

Sorry for all the questions, but having recently converted from another tool to Project, there are times when the costs of providing the data far outweigh the benefits achieved. For example, we determined that MS Project Server data using consistent enterprise resources across all schedules would start with our conversion date because the manual effort needed to fix all that past data wasn’t worth it.
I’m trying to understand if your issues are with current schedules and remaining work moving forward or if your issues are with attempts to convert past, historical data.

Theoretically, if you change the local resource name to exactly match the enterprise resource name, when you save the schedule to the server, project should recognize this match and ask you if you want that local resource to become the enterprise resource and if yes, it replaces the local with the enterprise resource for the entire spectrum of the project, which I think should cover past actual work as well.

One other thought that could be impacting how project schedules resources in the enterprise server environment that wasn’t a concern in the stand alone environment. Unless you tell it otherwise, Project will level the resources in your schedule against ALL other schedules in the server. Meaning, if Joe is used in your schedule and he’s fully allocated in another schedule for two years, Joe’s tasks in your schedule may not start any earlier than two years from now.
This can be turned off as follows. This is how using Project 2013.
In Project, Click File > Manage Accounts, and then select the “Choose an account” radio button. This tells Project to display an account login screen when the desktop software is trying to connect to the Server. Then close Project and re-open Project. You should now see an account login window appear. In this login window is an option: “Load Summary Resource Assignments” and this needs to be un-checked. Once un-checked, Project will now schedule your enterprise project resources based solely on their use within the open schedule.