Tubeless vs tubed to me is about how much work you like to do on your bikes. If you don't like messing with you bike, I say stick with tubes. (I have tubed and tubeless set ups)
If you don't mind a little bike attention then get tubeless.
Most people need an air compressor to seat a tubeless bead (extra toy for some folks). Or if you are lucky, a high volume floor pump may do it. Some people need to soap up the tire to seat it, a little messy.

You need to add sealant into tubeless tires, anywhere from 3 months and up. I think mine was pretty dry after only 3 months. You can either unseat the tube to clean out the dried up "snot" or you can just take the valve out and and more sealant. I poke an old guitar string into the valve to see if any sealant still remains.

So there is more work in the initial setup of tubeless, but if it helps you get less flats and you like the extra traction/cushness, that might negate all the work. On the flipside, I have used slime tubes and they have worked for me, especially in Southern California, with thorns.