[Bug] Plugin updates fail silently and version visibility is poor

**Bug Description**
plugins dont update easily, sometimes the update isn't done, very anoying.
moreover in the cli it is hard to see the plugin version

**Environment Info**
- Platform: darwin
- Terminal: vscode
- Version: 2.1.270
- Feedback ID: 738cc441-738d-4020-ba4b-1005a2509597

**Errors**
```json
[]
```

Start by reproducing a plugin update on darwin in the VS Code terminal using the reported version, then inspect the CLI's plugin update and version-display entry points. Done means failed updates produce a visible error instead of failing silently, and the CLI clearly shows each plugin's version.

Written by the indexing model from the issue text.