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So I have halo sas rims with maxxis rubber. I've had tubeless work on the rear but recently blew a hole in the rear type overjumping a gap, only small but the gunk wouldn't seal the hole. Every time I've removed the tyre before the gorilla tape inside has stuck to the bead of the tyre. The internal rim width is 30mm and the thinner role of gorilla tape doesn't cover enough of the rim so I cut down a wider roll and the tape comes up to a little below where the bead hooks into the rim.
If I don't put the tape that wide then the tyre fits too loosely on the rim to inflate (only got a track pump) and it just annoys me that it's hit and miss. I haven't yet repaired the hole in the tyre but it's only a mm or so hence my uncertainty at why it wouldn't seal with plenty of sealant in, air just kept pissing out.
I assume I won't get the tyre to seat again with even a little hole in it as it needs the pressure to build up (right?) but am unsure that the tubeless insert tool and worm thing would even fit in without making a far bigger hole (funny I know...). Sick of having to retape the tyre with half a roll of gorilla tape (takes 2 or 3 loops round) every time I take the tyre off.
I'm guessing the rims aren't meant to be tubeless and you're doing a ghetto conversion using gorilla tape?
The plug for the holes in tyres is meant to be a tight fit so it wont matter if it makes the hole a little bigger. You also will never get the tyre up unless it will seal up and be able to apply pressure to the sides of the rim properly.
I would try taking it down the local garage on their air compressor and popping it up that way, quick inflation makes it much easier to seat awkward tyres for tubeless.