Getting new tyres to form an initial seal and then "pop" over the ridges on tubeless rims is the biggest problem for most people/equipment. Wet or dry fit is debatable, but the sealant does act as a lube on initial fit, in my experience many tyres don't fully seat (pop) until 100 psi plus - then let them down a bit!
Learning what worms etc will/will not fix is worthwhile, carry a spare tube and tyre boot for the cuts that are not fixable (either operator error or simple reality), tyre boots made from bits of old tyres will bond with the latex compounds and fix the worst flint cuts I have seen but should only be used with a tube.
Tubeless tyre removal is always messy - latex sealant gets everywhere.
Valve cores do get clogged up with sealant, I keep the cores from knackered non tubeless tubes.
Running a tubeless set up on non tubeless rims is possible but without the ridges in the rims, when they lose pressure they will unseat the beads and be impossible to re seat with roadside inflation technology.
I abandoned tubeless and reverted to tubed, no regrets - I do have the compressors to make initial fitment easy (35cfm with 100litre reservoir), I just hated tyres that were always soft/flat and only stopped leaking about 30psi.