I think I can fix the issue with Google Chrome Portable not loading extensions?
I also upgraded from 139 to 140, but all my add-ons are still there.
First, delete everything in the [Data] folder next to the app in the portable version of Google Chrome. Please save your Google Chrome data beforehand to avoid losing it.
Then restart Google Chrome, log in to your Google Account, and sync your data. Once the sync is complete, all your existing add-ons will automatically load and install in Google Chrome.