When comparing herbstluftwm vs Wingo, the Slant community recommends herbstluftwm for most people. In the question“What are the best window managers for Linux?” herbstluftwm is ranked 13th while Wingo is ranked 42nd. The most important reason people chose herbstluftwm is:
Configuration of herbstluftwm can be done live in the command line, so no booting in and out of the desktop is necessary.
Question Ranking
Pros
Pro Can be reconfigured from the command line while it's still running
Configuration of herbstluftwm can be done live in the command line, so no booting in and out of the desktop is necessary.
Pro Uses a simple bash script for configuration
The configuration file for herbstluftwm is a bash script and is easily configurable.
Pro Offers a combination of manual and automatic tiling
Users can set up auto-tiling per app, or they can change any application to manual tiling to where they want on the screen.
Pro Highly customizable
Different layouts can be used in different frames on the same workspace, so the user can customize their layout to their liking on the fly.
Pro Great multi-monitor support
Herbstluftwm has built-in multi-monitor support that can customize to any size desired on the screen. This implies that the user is not held back by being forced to use each monitor's size.
Pro Pretty
Pro Support for both tiling and floating
Pro Easy to configure
Configure through the several test files.
Pro Multi-head support
Pro Easy to use
Cons
Con No single window floating
The user cannot use floating for dialogs or anything else without making the entire workspace float. Their only choice is pseudo tiling.
Con No system tray
There is no system tray support in herbstluftwm. In that case, users who wish to have one must use an external application.
Con Default startup config has something a bit annoying
You'll know what this means when you get it, but you can get rid of it. Reminiscent of old Windows versions and Nokia phones.
Con No "modes" like in i3
This would be useful if you wanted to turn the brightness up. Having it set to: Super+b; k; Esc. You can't do this in Wingo, although you could make a script to do such a thing.