wlfaws I have no clue which repo OS108 is currently using for the pkgin binaries.
Also, you didn't mention which pkgsrc tarball you used but,...
...what's happening here is a mismatch between the pkgs versions in the binary-repo (if you prefer pkgin) and the source-repo (pkgsrc).
You should use binaries compiled against the same source code version, i.e. if you're using a Q-release of binaries, you should use the same Q-tarball of pkgsrc.
Also, you didn't need to reinstall the OS, you could simply clean-up the mismatched pkgs.
Disclaimer: I don't use wine but, as explained above, the problem you're having is not specific to wine.
Edit: Let us know if you need help fixing your repos. If so, provide the URL inside /usr/pkg/etc/pkgin/repositories.conf and your physical location (country or even continent will be enough).
The binaries for 2020Q2 are not out yet, but maybe in a week or so they should hit the repos.
