It depends on the time/effort/cost/aggravation that you have dealing with tubed tires.

I'll admit that there was a definite learning curve for me, when transitioning to tubeless, and it was a little frustrating. Now? Not a friggin' chance that I'd go back - it is, on the balance, much, much less hassle for me.

That said, if I was one of those folks that only got two flats per year - no, I wouldn't bother looking at tubeless.