It's going to depend on where you live, if you are milling yourself, if you are importing or growing your own grain, and other factors.
https://saanichtonfarm.com/ is a local-ish to me farm that sells wheat, barley, lentils, and flour. Both direct from the farm and in shops. So it can be done.
Why so tightly regulated compared to other produce like zucchini? Historical, there are three big issues the authorities worry about. Keeping these in mind helps make it easier to get the documentation needed to sell.
1. Ergot, hunter (or one of the rodent based ones, I can't remember which), or other deadly stuff that can happen when grain is stored incorrectly
2. Cross contamination if more than one thing is milled in the same facility
3. Adulteration. In times of strife, it's common for suppliers to add inedible powder to flour which reduces trust in the food supply.
Basically we are being punished for the stupidity of those who came before.
But, take care of those issues and the red tape is pretty easy to deal with.
....
When I was looking into it, I looked around to see if anyone was within a days journey and already selling. I bought them a coffee and asked questions about what the local requirements are. If you can, start there as it give you an idea of your local conditions.
My conclusion was that their wheat was better than the stuff I grew, so I didn't take it any further. But I learned a lot. It's a very interesting aspect of food production.