I have the same concerns about going tubeless. I understand your cautionary measures. But I decided to try tubeless recently and so far my luck has been good (cross fingers, toes, arms, eyes, etc.). I don’t relish putting in a tube and dealing with the sealant everywhere. There’s another thread that talks about what to carry in a saddle bag with tubeless tires that I found informative. I’m going to adopt some of the recommendations. the forum discussion title is:
Road tubeless tires - What’s in your spare kit?
Give it a read. I’m new to tubeless tires too and am looking for any ideas that will make me feel more comfortable when I’m 20+ miles from home and my wife is at work.