1st tubeless experience was with Hunt wheels which came set up tubeless - 28mm Hutchison Sectors. Since then I've replaced the rear tyre with no problems getting it set up tubeless again.
2nd experience - had the lbs rebuild commuter wheels with Mavic tubeless rims. I set up these up myself with 28mm Conti GP5000 tyres with minimal problems getting them on and sealed - though I do have the Specialized air blaster to get the tyres seated.
3rd experience - my new Orbea Gain came with tubeless ready wheels and tyres, but set up with tubes. I had a puncture early on with the original setup and could not get the tyre off to replace the tube out on the road, nor after I got home. I eventually cut the tyre off. This was a tubeless tyre on a tubeless rim - and therefore a tight fit, but set up with a thick rim tape used, which made the tight fit even tighter, coupled with a lot of grip between the bead and the rim tape. I then tried to move to tubeless with IRC tyres. The rear I managed fine, but the front I could not get the tyre mounted and even the lbs took two of them to mount the tyre, and in doing so damaged the rim tape, so it would not seal properly. The IRC came off and an old Hutchison went on and sealed with no problem.
So getting a tubeless setup can be awkward, the level of difficulty very much depends on the rims and tyres used. Some combinations can be relatively easy, and some can be quite hard.
The bonus is that the ride is a step up from what you get using tubes, and the likelihood of punctures is much lower. I've done thousands of miles on tubeless tyres and have yet to puncture (as far as I'm aware). But then again, I didn't exactly have a lot of punctures when using tubes. But I like trying out new things and tubeless was an obvious challenge - which I'm glad I attempted.