On the tubeless thing…2 things.
1 - the fit is SUPER important. I set mine up so tight that they hold air even when the bead is pushed all the way into the center channel. You can test this pretty easily by just putting 10psi or so in, and just mashing the side of your tire with your thumbs sideways.
2 - just get foam inserts. Pretty much eliminates all of the paranoia and downsides of tubeless…plus I understand there are some ‘suspension’ benefits as well.