My experience is that once you have mastered the learning curve they are not much more trouble than regular tubed wheels. My Damone came set up with tubeless. Here are the things I learned pretty quickly.
If I ever flat on the road I will use a tube to get me home which will require removing the tubeless Presta stem. Not a huge deal.
The tubeless valves will easily clog with sealant making it difficult to add air sometimes. This requires removing the valve core and messing around with it. Not a huge deal but worth noting esp. if you need to add air and don't have a core removal tool. Apparently some valves are better about this than others. As it is I use a very small drill bit or pokey tool to get the sealant out so I can add air.
I was able to use a simple track pump to seat the bead. Probably not true of all tubeless tires but mine worked easily.
Adding and removing sealant is much easier with a sealant injector tool. I bought a Park version for about 20 bux because frankly .....Im a Ho for Park Tools.
The verdict is still somewhat out because I am limited on experience and I like working on things so learning the set up was fun for me. 300 miles with no flats on the road and these tires look like they will last a while. I will add new sealant either the end of the year or next season.