The packages you build from ports and the packages you install with pkg_add(1) are functionally the same. Building ports only consumes time and resources, and you also have additional packages built and installed that are build dependencies but not run dependencies.
The portupgrade tool you are missing from FreeBSD does have an equivalent replacement. After upgrading the OS, the OpenBSD admin merely upgrades all installed packages with pkg_add(1)'s -u option.
If you insist on building everything from ports, you may find OpenBSD's Distributed Port Builder dpb(1) very helpful, even if you are not building thousands of ports on a server farm, but only dozens on a single system. The dpb(1) binary is in /usr/ports/infrastructure/bin. While the tool by default builds the entire tree, you can create a pathlist file containing just the ports you wish to have built.
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