~7 years ago I started shaving my head. I do it every 3-7 days, so it does require regular upkeep. And at 7+ days it's quite annoying to shave at that point because the razor clogs quickly, maybe every couple inches. Probably would be better to start with an electric razor or clippers first at that point.
I tried to use a app that would simulate a shaved head, it was pretty rudimentary and I ended up looking pretty goofy in the simulation, because it used a very smooth ball shape, in reality it doesn't look goofy at all.
It does also mean you gotta wear a hat or sunscreen if you are out in the sun.