I am still very new to OpenBSD, but I have installed older versions, starting around 6.5, and upgraded all the way to 6.7.
My experience is that I consistently have issues getting pkg_add -u to complete as it usually hangs around 68% and I have to interrupt with Ctrl+C. When I then run pkg_add -u again, it completes stating everything is up to date. Running pkg_check after that says everything is ok.
For the upgrade to 6.8, after completing the upgrade I changed the /etc/installurl to a different one and the pkg_add -u completed without issue.
At my next upgrade I'll instead try using the -Uu options to see if anything changes.
Despite all of this, I haven't had any issues with the OS, itself (just my fat fingers and misconfigurations).
Note that the only packages installed are nano and dokuwiki plus their dependencies.
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