I had a puncture on the rear of my Fatboy, got it plugged as the tyre still had about 6,000 km more wear left in it & I'm Scottish! I checked the pressure every time I went for a ride & my thought was if the pressure had dropped a bit then it was time to replace the tyre. Ended up wearing the tyre out, but never felt at ease so think if it happened again I would just put a new tyre on, like PB said $300 + would be cheap compared to the worst case scenario.
Fixed the rear tubeless tyre on my deuce using one of those emergency plug kits from SCA in order to get to a lunch with Winger. Lasted the rest of the life of the tyre, another 10k or so. I was checking the air pressure regularly.
Riding this wave of success, I used a can of spray sealer on the tubed front tyre after a puncture to get from Clare to Adelaide and up to Mannum the next day for another lunch at which stage the tyre shit itself in a big way. Popped another can in to get to civilisation and the front end looked like a catherine wheel spraying liquid rubber all over me and the bike MIssus ended up meeting me with the trailer.