I’m using libdaisy and DaisySP on Mac OS 10.14.6, programs build and run just fine, but I find the Web USB loader inconvenient.
What command line program is used to flash the Daisy over USB?
Nevermind - I looked at how DaisyDuino does it, using stm32CubeProg.sh.
Is there some reason why you wouldn’t want to use proper programmer and enjoy the bliss of debugging? 
Not really, though I did work as a C programmer for 25 years, and seldom used debuggers.
What IDE and debugger are you suggesting for Mac OS?
I’m using St-link v3 mini + openocd + VS code + cortex-debug plugin on Linux, pretty sure that there were people using same combination on MacOs.
I am not ruling it out, but it’s a whole bunch more stuff to clutter my system. It’s already got multiple STM32 tool chains, several versions of Eclipse, Arduino, Espressif toolchains, st-link, Axoloti (and its STM32 toolchain). It’s already a bit of a nightmare.
Totally agree with you on toolchain proliferation. And if you use Arduino it’s a real PITA to move between the different targets.
In case you are using the Makefile approach you can just run make program-dfu.
I second this. I left behind the web programmer because I had to reload the page at each new binary flashing (with same name).
Now I use make program-dfu. It’s very simple on linux.
I found out about ‘make program-dfu’ shortly after looking at how it’s done in Arduino. Exactly what I was looking for.