I much prefer tubeless these days especially on the commute as I can run much lower pressures, this can make for a comfy ride over the nightmare roads of cardiff.
Over the past two and a half years or so I've had two punctures which didn't seal by themselves, once was this year where I had old sealant in the tyre and the tyre was worn and needed to be replaced, the other was on a commute and both times I believe there was a fair chunk of glass in the tyre.
Both times I was able to dislodge the glass, reinflate the tyre with effetto mariposa espresso and make my way home at lower pressures;
http://www.effettomariposa.eu/en/products/espresso/I'm currently trying Orange Endurance Sealant as I've always used Stans, users report better sealing properties with the orange.
The tyre should be a bit of a pain to fit first time around, if not then you don't have enough tape around the rim as the idea is that it sits correctly on the rim and shouldn't blow off. I've actually had a harder time fitting Conti Gatorskins than tubeless.
The following is supposed to be excellent for mounting tubeless;
https://www.sjscycles.co.uk/tools/koolstop-tyre-mate/I've found tubeless to be pretty much the same as regular tyres and they do appear to stretch over time, therefore easier to remount at a later date should you need to.
You can also carry the following which should assist you if you have a nasty puncture, the tyre lever would replace you existing ones and the worms are tiny so there's no real weight penalty;
http://thecycleclinic.co.uk/products/var-rp42500-tyre-levershttp://thecycleclinic.co.uk/collections/tubeless-bits-and-bobs/products/genuine-innovations
