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I've converted to tubeless this season and have been very happy with the switch. I've had one catastrophic failure where a stone tore the sidewall and left an inch long gash in the tyre, that sealant was never going to fix but that's it.
I do like the ability to run lower pressures than clinchers too, as it affords much more grip in most conditions. I've also raced a fair bit on them and have been happy with the performance and convenience and haven't had a single burp (which is a common-ish problem).
I have been using tubeless specific rims though, Stan's Iron Cross.
So it's worry going tubeless again then by the sounds of if.