I am running tubeless on all three of my bikes now and have found it to be a mostly positive experience.
I have a mountain bike with mahoosive 27.5+ tyres and two road bikes running 28c. I use the original Stan’s sealant and have used a Stan’s Dart a couple of times for sealing large holes.
I’m also going to convert my wife’s bike over to tubeless, as she and the rest of her group of lady riders seem to be totally unprepared to even attempt to change an inner tube.
So I’m thinking that at least there’s a chance that any puncture will seal itself immediately, or with the aid of a Stan's Dart, and I won’t receive an International Rescue Callout phone call.
I do think that for anyone who has a problem with removing a wheel and getting a tyre on and off for whatever reason, then tubeless is definitely the way to go.
Paul, I used to do this as well, until I realised that my releasing a small amount of air was encouraging sealant into the valve core as that is what it is designed to do with any release of air. I also use a screw on Lezyne track pump and now, after unscrewing the valve core nut, attach my pump without releasing any air. It takes a bit more of an initial effort to open the valve, but it is only ever open with air flowing in under high pressure so there is no chance of sealant fouling the core.
I also use a valve core tool to fully tighten the core as I also used to experience the problem of removing the core when disconnecting the pump. Back when I used to run tubes I also carefully applied a small dab of superglue to the core threads before inserting.