I think the amount of times the user is allowed to trip should be proportional to the intensity with which the user is going to use the tool. If the tripping en

I think the amount of times the user is allowed to trip should be proportional to the intensity with which the user is going to use the tool. If the tripping enables advanced use, of course, which is not the case in your example. First time use is completely different than prolonged use. Efficient use is not necessarily the same as ease of discovery. The first time I rode a bike, I fell off. Does that mean bikes are badly designed? I get the feeling most designers who make an effort only look at that first time use. I get it, if the user comes around only once a month, your product should be super easy en intuitive. But if it is used daily, your product is a tool and is allowed to require skill to master. If the end result is better in some way. Either because it is more efficient, or because it takes time before one sees that there is actually more logic in that interface than you thought the first time you used it.