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A. You don't need to download all content but make sure to create a backup following these steps:
B and C. As you are moving drives, I would recommend first deactivating your licences and then proceeding with uninstallation:
Move or Deactivate License Keys - Tableau this also tells you about the .tlf and .tlq files
D and E. The upgrade you are gong to perform is a major one so make sure you read about all the changes and requirements (such as the need to stop refreshes). This blog highlights the changes to Server https://www.theinformationlab.co.uk/2018/07/25/15-big-changes-coming-to-tableau-server-2018-2-on-windows/ and since you are changing drive look at this: Upgrade Tableau Server in a Non-Default Location - Tableau.
F. Tabcmd has been replaced with TSM.
In summary, do plenty of research to prepare for the upgrade. There are plenty of troubleshooting pages too if you get stuck somewhere.
Hope this helps.