Upgrade Windows Server and preserve UNC paths?
Solution 1:
It will take some transition work, but the first thing you should do is strongly consider using a DFS Namespace for your domain. DFS lets you have a single directory that links off to various file servers and shares underneath. You can easily retarget the links to a new server at any point, and this will be transparent to the user. But if you aren't already using DFS, then this will require making disruptive changes, but once you have made them you should be good for a long time.
The other thing that can help in a migration is to use a DNS alias to redirect the DNS name that used to be belong to the old server to the new server. This does take some work though. See this question.
- How to Configure Windows Machine to Allow File Sharing with DNS Alias
Solution 2:
Assuming you are not looking to do in place upgrades, most of the common roles can be migrated using the Windows Server Migration Tools.
Many roles and features can be migrated by using Windows Server Migration Tools, a set of five Windows PowerShell cmdlets that was introduced in Windows Server 2008 R2 for easily migrating role and feature elements and data. The migration guides support migrations of specified roles and features from one server to another (not in-place upgrades). Unless otherwise noted in the guides, migrations are supported between physical and virtual computers, and between full installation options of Windows Server and servers that are running the Server Core installation option.
There are other ways, of course but the migration tools are a supported method