So this is my story with going tubeless.
I took the plunge and decided that this fall I wanted to setup my cross/gravel tires tubeless, since I had to buy a new pair of tires anyway. I also commute on the bike and suffered a lot of punctures last winter. Real cross tires seems to not have any puncture protection. Turns out It’s not really needed in the grass and mud and traction is the main concern.