For many this is new tech, so it may be that we are all learning more about tubeless systems and it sounds like
@PaulSB has unfortunately gone the wrong direction in some of his choices.
For floor pumps, I find the Joe Blow with the flip head to be much less hassle, as you have no risk of unscrewing the valve cores. With tubes, I had moved away from Continental tubes as they sometimes let me down road-side when dealing with a puncture and the core unscrewed as I removed my pump.
Some sealants seem to be better than others for use in road tyres. Many sealants seem to have originally developed for MTB tyres which run at far lower pressures than even the reduced pressures that tubeless enables on road. I'm using Caffelatex sealant and have been using it for about a year on various bikes. No need to remove the valve when using the syringe to fill. No issues with sticking valves despite regularly checking and adjusting pressures.
Plug kits. Worms are cheap, if you're paying £40 I hope you got a very bling capsule for it and it came with all the tools you need. The tools should include a reamer so you can enlarge a pin-sized hole to allow the sealant (and its fibrous admix) to flow into the hole and then seal. If the hole is too small, air gets out but the fibres cant get into the channel and plug the flow.
Refitting tubeless tyres after inserting a tube at the roadside, hopefully a last resort, but often that comes down to technique of fitting tyres. If you need lubricant to get the bead over the rim, saliva works well.
I'm happy with tubeless and I'm gradually converting more of my wheels over to it. These some usefull information here:
https://thecycleclinic.co.uk/pages/tech-page and
https://thecycleclinic.co.uk/blogs/news/living-with-tubeless-tyres