What Mitch said: It gets easier, faster and far less messy when you’ve done it a few times.
Judging tubeless by installation only is being short-sighted. You can’t know how much aggravation in the field you’re saving yourself by dealing with it in the shop. By my experience, goatheads, pinch flats, road debris and inner tubes are more high maintenance than tubeless.
“That leak” – ? If you keep the wheel oriented vertically and are using tubeless gear, you should not get more than a few drops of sealant anywhere. If you have sealant gushing out of somewhere, something is very wrong. Did you check out a video tutorial like the one at the Stan’s site?
It’s a happy union here. You can learn to love, too. : )