With each mounting of a new tire, I'm convinced that the biggest factor in a seamless experience is... experience. It just trends towards easier each time, even when revisiting tire/rim combinations that were hellish previously. If I were to provide bullet-point advice for a tubeless n00b, in no particular order, it would be something like...
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• If you're going to give up at the first sign of adversity, don't bother.
• It doesn't work without maintenance, so make maintenance easy. Set reminders on your calendar. Go through the valve rather than breaking the bead. Have a valve core tool on-hand. Use a dipstick. Top off through the valve. Have extra valve cores around for when they get gummy. The process only takes 10 minutes if you're set up properly.
• Rotating tires is more work - I buy tires three at a time so that I can keep the front tire on the front while wearing through two rear tires. If you really want to rotate, knock yourself out, but I'm done with that.
• When fitting the tire to the rim, do the little things. End at the valve. Get the beads in to the rim bed channel from the start and regularly check to ensure they're there through the end. Take up slack regularly. Doing this, I've never had to use anything besides my bare hands to mount tires.
• When seating, do the little things. Have a bottle of soapy water on-hand. Mist the tire beads all the way around, on both sides. Pinch and wiggle the tire all the way around - you're making sure that the beads are in the channel and that the beads/rim are slippery enough to pop up on to the shoulders when you hit it with air. Access to a good compressor or air blast canister really helps. A "snap, snap, POP!" is the sign of a job well done and is *so* satisfying.
• After seating a tire, deflate it - if the beads don't stay in place, you didn't do it right. If the beads do stay in place, remove the core, add sealant dose through the valve, re-inflate. Shake and spin the tire a bit so that the sealant can plug any little leaks. Check pressure a little later - add more air and spin if necessary.
• Get plugs/bacon strips and keep them in your riding tool kit.
• If your sealant isn't permanently sealing the vast majority of your punctures at your riding pressures, get a new sealant.
• Valves with conical rubber gaskets have worked better for me than the more fancy one with saddle-shaped gaskets made to sit in the rim bed channel.
• Anticipate that you'll make a little bit of a mess. If I'm in the house, I put a puppy piss pad under the wheel. Keep paper towels/rags nearby. The bottle of soapy water lube is great for clean-up, too.

Not a comprehensive list, though it actually looks like more work than it really is - I'll add if I think of other nuggets. Other people will have a different list and your mileage will vary, obv.