I have been running tubless since 2004. Have not had a flat since. I have done 3 24 hour races with no flats, as well. In the summer and fall, I try to ride 3-4 days a week but that has tapered off with the little ones the last 2 seasons.
When I started early on with tubeless, I ran low PSI and had issues with hitting a feature hard and popping the tire off the rim. Now I just run normal 38 psi and about once every 2-3 months change the stans fluid.
I carry tubes just in case...I sometimes get back from a trail and see little pin wholes with moisture, which I interpret as Stans doing the trick.
My rims are designed for tubeless but like Rudy said you can do a conversion on standard tubes, as well.