Honestly tubeless isn't that hard generally. There are some rim and tire combos that can be a right pain.
On my mountain bike, I don't find putting tires on any harder then tubes. Put it on as you would with a tube (just minus a tube), inflate with compressor until it pops in place, take the core out of the presta, inject sealant. Done. It can be a bit more messy on trail repair but imo no harder then swapping tubes. Downsides, tires need to be air up more often in my experience, sealant needs to topped off occasionally, presta valve cores sometimes get gummed up and need to be replaced. Upside at least for me about a 100x times less flats. I can think of one time I needed a tube and couple where I needed plugs. Before I went tubeless, I was changing tubes about once a ride or pumping up the tires pretty rock hard.
That being said I have tubeless in my gravel bike and to be honest, I don't think I really need it. So probably going forward I would probably only run tubeless in bikes that see singletrack.