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Obviously never owned a pair of TB14's then ;)
When @Howard says tougher to work with than their traditional counterparts he means TB14's are rims for real men with strong hands. Very strong hands...
Howard knows a lot more than me about tubeless but I've read some tubeless ready rims seal a lot more easily than others. The Stan's I'm looking at are supposed to seal really easily, for example.
"are tubeless rims more annoying/painful for installing normal tubes/tyres on?"
Not unless you do something silly like use traditional rim tape.
Wide rims are tougher to work with their traditional counterpart. Maybe. I find getting the same tyre on a TB14 tougher than an open pro for example