The last 2 seasons i have ran tubolito tubes which seem to be fairly resilient to pinch flats. Running low pressure and even hiting stuff hard enough to flat spot a rim, no puncture. 2 seasons, no punctures. Running tubeless this season for the reason I want an insert to protect the rim I put a heap of hours into polishing and don't feel like ever doing it again...
The only thing I don't have experience with is tubeless and tire inserts. Without inserts tubeless has been completely unproblematic for me. I was so happy when I could switch my sons MTB from 24" to 26" so it could run tubeless. Finally no pinchflats anymore every month!
One could, of course, run a high pressure to avoid pinch flats. But being to able to run low pressure improves comfort and traction significantly.
There are many technical aspects of MTB bikes that are discussed here on happy and that people have different opinions on, tubeless is usually not one of them.
PS: nice chatting with you on Saturday!
EDIT: Now I thought a bit more, I wonder how a tubolito could help. You should be able to replace the tubolito by tubeless and run at the same pressure without pinch flats or run an even lower pressure.