With Stans Crest, Arch and DT Swiss rims, a lot depends on the tyres. I find the newer ones better.
I’ve struggled with non-tubeless Continental (a visit to the garage and 50p well spent) and Kenda.
Maxxis non-tubeless were better. Schwalbe and Maxxis tubeless-ready have been fine.
I always inflate them dry.
I got the bits together for a coke bottle inflator, but since I bought a Lezyne Digital Overdrive pump, I haven’t needed to put it together. I had an Edinburgh Bicycle Revo before, but the Lezyne shifts more air and is better built.