There is a small learning curve with going tubeless. It was pretty messy for me at first, but as my technique improved, the mess diminished. Now I can install a new tire or refresh sealant, which I do about every six months, with no mess at all. (I write down when I put new sealant in for each of my bikes so that I can keep track of how long it has been).
I can get tires to seat with a floor pump 30-40% of the time, pumping like fury for about 15 seconds, by which time the tire will either have begun to seat and I keep going, or nothing is happening and I'm setting up the air compressor, which works 99% of the time. Either way--pump or compressor--removing the valve core first creates better air flow into the tire. You'll lose that air when you remove the chuck, but the bead will be seated, and you'll be letting that air out anyway to add sealant. You know the bead is seated when you hear two or three pops. Such a satisfying sound.
I use a syringe that screws onto the valve stem, but I don't use the plunger (sealant can actually seal the syringe tube as it flows into the tire. I once pushed the plunger hard enough to try to overcome that blockage that the syringe tube popped off of the syringe, spraying sealant everywhere). If the sealant stops flowing, I push lightly on the tire, which sends air bubbling back up the syringe, unblocking the tube and allowing sealant to keep flowing. I might do that two or three times, and then the syringe is empty. Refreshing sealant in a set of wheels is now about a five minute job.