With the changes from Tabadmin to TSM in windows, there has been a lot of confusion and lost time over the changes to the way that uninstallation of the product works/ the obliterate script.
Using Add//Remove programs to uninstall a version of Tableau Server 2018.0 or newer (TSM) before upgrading to the newer version creates a state that is unrecoverable, and requires using an "obliterate" script to recover from. Obliterate removes all traces of the specific version of the product, and requires starting over with the upgrade. In addation, failed upgrades due to confusion over documentation, miss-typed passwords, port issue, and other miss-configurations leave the server in an unrecoverable state, which requires again, that obliterate script to be run.
In these scenarios, an attempt to re-install the software does not error out immediately- but makes it a chunk of the way through the upgrade before failing with one of a number of errors (none of which point to the previous uninstallation as the cause of the issue)
I propose a few mix/match options that might help
1) A warning on the add/remove programs uninstall process that notifies users not to use the add/remove program process to remove the software from the machine, and suggests the obliterate process instead.
2) A pre-install scan that checks to see if there are previous uninstalled versions of the software that need to be addressed before continuing with the upgrade, and gives the specific versions that are partially or improperly installed/ steps on how to resolve the issue.
3) An overhaul of the uninstall process that allows it to function the way that previous instances of tableau server did: Uninstall removes the software, but leaves setting files and/or data, and obliterate removes everything (obliterate would be the TSM version of a "clean uninstall" in previous versions).
4) Improvements to error messages that give a direct indication of what the underlying issue is
Please suggest other options, as there are likely lots of ways to solve this problem!