I picked up a 2022 Caledonia-5 in August with the same tires and DT Swiss 1800 wheels. After 3 flats from in the first few hundred miles, I converted to tubeless. I didn't have any problems breaking the bead while replacing tubes.
I had no problems breaking the bead when I removed the tube and installed the (included with bike) tubeless valves. It was fun watching sealant spew out of the holes as I inflated the tires after conversion. All holes sealed within seconds.
In the past three weeks and 500-600 miles, I would have had four more flats. All but one sealed almost immediately. I picked up a nail that took about a minute to seal as it spewed sealant all over my bike. I aired up and continued on. I carry a tube just in case, but I just added a bacon strip repair kit for some more insurance.
I'm now a big fan of tubeless tires.
Not sure what it is about these Vittoria Rubinos. I put over 4000 miles riding my Specialized Sirrus hybrid the same routes I ride now and only had swap tubes a couple times.