I started with 3.6.5 and currently have 3.8.4PL2. I've never had to "undo" something during an upgrade because the later version overwrote the earlier version.
In fact, I'm pretty sure I had to manually turn on the Social Groups, Photo Albums, Visitor Messages on Profiles, etc that were introduced in the 3.7 series after making appropriate usergroup permission edits.
You can always copy your 3.6 database to a test database, upload 3.8.4 to a test folder, config 3.8.4 to read your copied database (you can copy the 3.6 config and edit it), and run a test upgrade.