Wow this sounds like a nightmare!
This is not my jam at all, im not an aggressive rider like PDoz, im just curious about the benefits of running tubeless, they would have to be substantial to offset this much hassle?
I did a search and it said tubeless allow you to ride at a lower PSI, there has to be more to it than that?
I couldn't care less about the alleged lower pressure on tubeless - in fact, I'd argue that tannus armor + tubes can be run at lower pressure than tubeless - at least with the sort of riding I do ( rocky mtb )
The reason I prefer tubeless is the quality of the ride -I've used same tyre, same bike, run tubeless, tubed, and tube with tannus and I believe I can feel the difference. I also swap wheels between bikes, and have started a ride and thought " yuck, that's the wheel with tannus" , or " better be careful, that's the wheel with a tube" .
Tubeless at the right pressure feels lively - the tyre reacts to rocks quicker, rebounds more consistently, and feels more consistent as it slides.
Slip a tube in, and there is friction between the sidewall and tube +/- about 100 gms more unsprung weight - yes, you CAN feel that ( at least, on my carbon levo sl with upgraded suspension dialed in well ) . It's more than just unsprung weight, though - I recently dropped 200 gms off the back with a lighter cassette , it felt more lively but not as much difference as I get by ditching the tubes.
Now, slip in tannus plus tubes and the ride is dead. It's like having 2/3 clicks too high on both compression and rebound, plus dragging the kids through sand. Still the best puncture protection I've experienced, but HORRIBLE ride quality. Perfect for the kids bike .....no fixing flats and a chance to keep up with them.....unfortunately they have learnt to fit their own tyres so I can forget about that.
BTW , I carry plugs, patches, and an ultralight spare tube. I don't carry sealant. Anything serious enough to need sealant replaced is going to need the tube- eg sliced sidewall . Or a big burp with the bead / seal breaking - it's easier to slip a tube in than trying to get the bead to seal using a hand pump!
Oh, as for fixing flats the easy way -My wife has an internal gear hub, she just carries a sausage tube ( can't remember the brand, but it's a cylinder rather than loop so can be easilly fitted without removing the wheel.)