How do I pick up and move shortcrust pastry dough without breaking it?
If the pastry is sticking to the rolling surface regardless of how well floured it is, it is possible that you are pressing down overly hard and not keeping the board floured throughout the process. 

These are the stages I use in rolling out pastry:


Shape the ball of pastry into a thick disc or rectangle using my
hands, to make it easier to get the rolling started.
Flour the surface well and make a pass in one direction with the
rolling pin make a quarter turn with the pastry and slide it about a
bit in the process to make sure there is still flour underneath.
(While your pastry is still quite thick it is easy to lift it a
little to scatter a little more flour under)
Repeat this process until the pastry is getting too big to more
about, but don't try to achieve a lot of thinning with each pass, much better to make more passes which thin the pastry a little each time than a few passes which thin it a lot.


If your pastry feels as it it is sticking once it has got a bit larger, use your rolling pin to pick it up to add flour. Place your rolling pin near the edge of the pastry furthest from you and slip the fingers of one hand under the edge of it to hold it eh pastry against the rolling pin, then supporting the pastry with your hand roll the pin back towards you so that the weight of the pastry is spread across the pin and lift from the board. if it is sticking you can use a palette knife to ease it free. Add more flour to your surface and roll the pastry back down.


Use this same technique of rolling the pastry onto the pin to
transfer the finished sheet to the pie-dish.