Do you have frequent punctures? How expensive is it to replace a tyre after a puncture?
If You're talking about tubular, I must admit they were for me the least reliable. I did a 60 mile ride on the Isle of Wight and noticed at the ferry there were several pinhole punctures, all sealed thankfully.
Ive had several pothole impacts which have put a big cut in tubular and this resulted in near deflation to the point it wasnt safe to continue.
Ive had probably just as many pinhole punctures with tubeless never a problem. I just keep riding knowing that the hole will seal.
The two occasions where Ive had major tyre damage, tubeless has saved me from a nasty crash. The first was coming down Mt Teide at 40+ mph, after 20 mins of descending I noticed a wet feeling on my legs. Stopping to look I saw a big gash in the tyre. I rode the rest of the mountain steadily to the hotel some 12 miles further.
The other time a mountain bike cut resulted in half deflation, but I heard the tyre let go on a descent. I was able again to ride back to the car albeit a bit slower without needing to repair