I use `less` with help output because if the help output is long, it starts me at the top of the help output rather than the bottom, and the top usually has a nice summary of the command usage that I usually want to read.
More importantly, I can easily find things by searching with less's `/` hotkey. Relying on the terminal emulator's built-in search isn't great because (a) I'm not used to it - I am more used to vim's keybindings, and the search hotkey `/` is the same in vim, and (b) that's also going to search all the output from before I ran --help (not as big of a gripe, but still somewhat annoying).
More importantly, I can easily find things by searching with less's `/` hotkey. Relying on the terminal emulator's built-in search isn't great because (a) I'm not used to it - I am more used to vim's keybindings, and the search hotkey `/` is the same in vim, and (b) that's also going to search all the output from before I ran --help (not as big of a gripe, but still somewhat annoying).