Try a new game just to see if that was what caused the problem with the portrait.
Once you get past Fort Joy, you will have access to a mirror that allows you to respec your characters. Using that will regenerate the portrait, since you can change appearance, as well (with certain restrictions for the origin characters)
You can email supportdos2@larian.com, with a link to this topic and the report.zip file (or a Dropbox or Google drive link, etc) generated by the
D:OS 2 Analysis Tool.
Extract the zip file somewhere handy (like the Desktop) and in the AnalysisTool_DOS2 folder, run corresponding executable. It should detect the game install path, but if not you can browse to the 'Divinity Original Sin 2' folder. Optionally run the tests first, and then generate a report (it will be saved in the same location as the Analysis Tool).
The report will contain system and game information, as well as your saved games. To greatly reduce the file size, you can delete all or all but one of the saves from the zip (double click the zip file to open it in Windows Explorer, then browse down to the ..\Savegames\Story folder).
The support server error should be fixed in a future update.
It can be caused by your ISP redirecting to a search page; in that case,
turning this option off can fix the problem.
In addition to what is in the FAQ (which I should update), you should be able to rename the SupportTool.exe executable in the install folder, make a copy of EoCApp.exe and rename it SupportTool.exe to continue starting the game through Steam.