It does require some confidence, because you're guaranteed a total loss if it doesn't work.
But the only way to find out is to try. There are 3 places you can cut in your average Echeveria rosette (in vertical order from bottom to top):
1. through naked (old) stem well below the terminal rosette
2. within the rosette itself, so that you get a cutting to root but also leave several healthy leaves on the plant
3. within the center of the rosette, pinching out the growth point
The first is the safest but the least likely to give you offsets to play with later. The second is where I like to make the cut if possible, because each leaf left attached to the stem of the mother plant can give rise to a new rosette, theoretically. When the leaves are packed really close together along a stem and option #2 is not possible, then you have to go for the gusto, or wait things out to see if the plant will offset on its own. The third is of course the most risky and the most likely to hit the jackpot when it works.
There's a book called "Succulents: Propagation" by Attila Kapitany and Rudolf Schulz (one of the volumes in a 3-part series if I remember correctly) actually published in Australia. That would be the best place to start for expert advice on this subject, if you're old school like me. The authors have written other books (Schulz an excellent treatise on Aeoniums which I also recommend), but this particular 112-page softcover book has all sorts of nuggets to offer on the subject of propagation.
