I’ve done it: I’ve completely migrated everything to OpenBSD.
My VPS’s and my daily laptop (t14s) now run barebones OpenBSD installs and I’m doing my best to stick to tools in the base install.
With OpenBSD sticking closely to base is actually doable:
vi works fine and can be configured to do 90% of what I used nvim for;
cwm works like dwm (but I’ll never give up suckless tools);
ksh is wonderfully stable and concise;
disk-encryption can be done through the installer;
pkg_add has a robust ports tree with all the software I need;
and all the usual xorg tools come pre-installed with xenocara.
Switching xterm with st and adding ungoogled-chromium (which offers unveil and pledge support), dmenu, R, LaTeX, &c. gave me everything I needed for a functional system.
Overall, installation is a breeze and gives you a boring system that only does what you need.
If you’re familiar with suckless tools and you’re on the fence about switching to OpenBSD, just take the plunge! Transition pains are minimal.