In my experience tubeless are more reliable and comfortable than tubed. Two years ago when I changed the tyres we found seven "punctures" that had self-sealed without me knowing it. That's seven saved roadside tube changes.
The initial set up can be a PIA. In my experience finding the best valves for my wheel was the issue.
My routine is to check tyre pressure before every ride. I've done this for decades. It's no more work than a tubed tyre.
If you get a hole which is too large to self-seal a plug will do the job quickly and permanently. Plugging a tyre is far quicker, cleaner and simpler than changing a tube. If the damage to the tyre is significant, I once put a 2cm slash in my tyre riding over broken glass, you're in no worse a position than if you had tubes.
Since going tubeless in spring 2019 I've had one major issue, slashed tyre as above, which required a tube. I was tired, rain pouring down, getting the tyre off was difficult, sealant mixed with rain everywhere. A nightmare. Yes, I was ready to bin tubeless that day.
Always carry a tube just in case the tubeless fails completely. Unlikely but it can happen just as with tubes you can be really unlucky and use all your spare tubes on a single ride!!
Today I use it on both bikes. Tubes are a thing of my past.
