SystemD and Wayland may be new life for Linux, but less so for Unix (BSD). OpenBSD's version of X11R7 (
Xenocara) isn't a problem and doesn't need fixing (for instance it runs X at a low privilege level such that the security issues associated with X are circumvented). Accordingly it will continue alongside Wayland/systemD type 'enhancements'.
twm/fvwm/cwm are integral to the OpenBSD base system, so will equally continue along. No thrills, but depends upon whether you need those thrills or not. I personally just want the window manager to load, position and decorate windows but otherwise be out of the way and twm (with its direct writing rather than via widgets) performs that task adequately well enough for my needs.
My setup is comprised of the base OpenBSD + firefox (which also serves as pdf viewer, calendar/diary and email), libreoffice, mpv (videos), mtpaint (image editing) and xfe (file manager and text editing). xcalc and other X tools compliment that sufficiently enough for my needs. 5 packages (around 114 units IIRC) on top of the base system (I use pre-built binaries provided by OpenBSD rather than building from source) ... that takes minutes to install afresh.
If it works adequately and ain't broke, don't fix it. Often 'upgrades' turn out to be downgrades. Wasn't it in Debian where a release manager decided to make a small 'improvement' change to the developers submission and in so doing left open a multi-year security flaw in something like SSL?