I run tubeless setups on all of my bikes including three road bikes, three gravel bikes and two mountain bikes. In almost 40K miles of riding I have never flatted a tire in a way that has required me to put a tube in. I have had to plug punctures twice, in bath cases with a Dynaplug which worked fine. So, flatting is not a problem for me.

I stopped riding with tubes two years ago. I carry a Dynaplug racer and a Cycplus AS2 Pro in a jersey pocket. I ought the Cycplus last year for about $80 and it's a great little pump. I find the Cycplus to be less fiddly than CO2, it works well with sealant and it can pump 3-4 road tires from flat to full pressure. I like the pump so much that I've stopped taking a track pump with me when I drive to a ride: if I need to top up pressure, I just use the Cycplus.