Yes it will, if you make sure that there is no lint between the crystal and the cyclops. The heat treatment works well, just be careful if you have a crystal with AR.
I think this is a good idea but to make it really work efficiently, these pictures, rep-ratings and great stuff like onzenuub's list of reviews (plus the actual reviews themselves) should all be moved to a separate "Rep-Review" section.
The reason for the higher cost is that you bought Bergeon tools. They are very good but also not cheap. Like with any tools you buy, you can go different routes. If you just plan to remove one link from a submariner bracelett, you don't need Bergeon screwdrivers. However, if you are serious about this hobby, good tools are paramount.
Have fun...
I have a CC and I love the rubber strap. The Carlos Coste rep is already a heavy watch and with a bracelett, it is will be more like a workout-weight. Remember that the gen has a Titanium case &bracelett, while the rep's case (and bracelett - if you can get one from another watch) is brushed steel.
On the other hand, you could very well have bought the gen rubber strap (of the Oris Diver Series) and have put that on your gen CC cause you liked it. Every once in a while I wear my gen Crosswind or B1 on a Breitling rubber strap, though none of the two are sold with it.
As said by Ds - the arrow indicates the direction in which the pin has to be forced out. To reinsert, reverse the direction. Don't try this without proper tools. They are not really expensive and you can use them for all your pin-based bracelets.
Yes, this should not be a problem. If you feel comfortable to uncase you watch, you can do this yourself - but I would recommend to have it done by a pro if you have no experience.