I've been baking pies and making pie crust from scratch for a good long time now. 15 years or so. In that time, it was inevitable that I'd learn a few tricks. Now really really good and proper bakers (like the ones who let their eggs and other ingredients come to room temperature before using them) will probably be scandalized by my tips. But it's what works for me, and what takes the frustration out of pie making.
For me, the biggest issue with making crust is the crumbly nature of the dough. The crumbs make it impossible to roll out without the edges cracking, separating, etc. So to combat that, here is my top secret tip #1:
Use margarine instead of butter or shortening.
My mother would be horrified. She's a butter purist. Maybe I will be too when I no longer have small children needing to be fed NOW, not when the butter softens enough to use. With margarine, the crust still gets that beautiful marbling and flakiness that it's supposed to have.
Make more pie dough than you will need.
For years and years and years, I struggled with my "Pastry for 2-crust pie" recipe from the Good Housekeeping cookbook. I was forever patching the edges of my pie crust after putting it in the pan because the edges always cracked. This did not make for very pretty pies and occasionally lead to the crust leaking so the pie stuck in the pie plate. So now I always make more crust than I need. (But I need to get better at rolling the crust thinner...since I have more wiggle room, I don't always get it thin enough.)
I still use the 2-crust recipe (above, left) as it is...when I'm making a pumpkin pie or something else that doesn't need a top. When I'm making an apple pie, I either do 1.5 times the recipe, or 1/2 of my husband's nan's pie crust recipe (above, right). That's the recipe she uses for her all-day apple-pie-making marathon. It's not crumbly at all, in fact, I think she actually kneads the dough a little. My daughter and I got to join her a couple of years ago and I loved being part of the tradition.
Do you make pie crust? I'd love to hear from you if you try my heretical pie-crust-making tips!