When Tiptop first released their kit in about 1981 our bike shop held an open day. My boss used a drill to put holes into an old tyre and customers took turns to fix them. Great fun and to prove that it works he then fitted the tyre to his CB900 and used it up.
IMHO tubeless tyres are the best invention since Mr Dunlop invented air-filled tyres. Having said that, this doesn't always work and you have to consider whether you will carry some kind of backup system, like tyre patches and the tools to get the tyre off and onto the rim.
Putting tubes into tyres on tubeless rims is asking for trouble, because it elegantly combines the disadvantages of both without the advantages of either: you can't easily get the tyre off the rim, but you have to do it for every puncture.
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