A few months ago, I created this illustrated guide to pie dough that you might find useful.
Making the dough: http://beyondsalmon.blogspot.com/2006/03/technique-of-week-pie-and-tart-dough.html
Rolling out and baking: http://beyondsalmon.blogspot.com/2006/03/technique-of-week-rolling-out-and.html
I am all for using machines (I use a kitchenaid mixer, but a food processor is fine too). If you freeze the bowl and all the attachments, you'll be fine.
As far as rolling over the pin problem... If flipping the dough over the pin and then unrolling it over the pan is tough (I assume it is cracking and braking), the dough might need a little help. Here are some trouble shooting ideas:
1) measure flour correctly. ideally you should weigh it. 1 cup = 4.5 oz. If you don't have a scale, stir the flour with a spoon to fluff it up, spoon it into a dry measuring cup (never scoop) and level off without compacting. You'll be amazed what a difference this can make
2) recipes vary in their flour to butter ratio. The ones that are really heavy on the butter are more fragile, so you might want to choose a different recipe. The one I use is 2.5 sticks butter for 3 cups flour.
3) When you cut the butter into flour in the first step, leave some butter lumps. It doesn't matter whether you do it by hand or machine, just don't let it get to the consistency of sand. Better have large lumps than no lumps.
4) The french technique of smearing the dough on work surface for final integration (see the pictures in the above guide) is very useful for ending up with the dough that holds its shape and is much more workable.
5) When shaping it into a disk, smush it this way and that to get rid of cracks around the edges. Smushing is not the same as kneading. Kneading will develop glutten and make your dough tough. Smushing will just make it stay together.
6) Don't roll out the dough right out of the fridge. It's much more likely to crack. Let it sit at room temperature for 15-20 minutes until it's no longer hard.
All this might be really hard on a hot day. Since I don't have AC, I wait for cooler days in the summer to make 3-4 pie crusts and freeze them.
And don't give up. Pies and tarts took me 6 years to master :)
re: A Fish Called Wanda
Crisco will make the dough more pliable and a little more tender, but I find that all butter is more flavorful. You can try to use crisco until you get more comfortable and then switch to all butter. Crisco does have trans-fats, which are not the best thing to put in your body, but if you make a pie once a month, I am sure it won't kill ya ;)
A food processor is a very rough & tough method of handly pie pastry. It works well for other types of dough but not pie. I suggest using a pastry blender until you become expert.
Consider chilling the dough for only thirty minutes before you roll it out. If it is very soft after rollig out then chill is flat for 15 minutes before you place it in the pan. I prefer to fold the dough into fourths rather than trying to roll it on a pin.
If you use a pastry cloth and rolling pin cover, its easy to get the dough up over the pin (lift the cloth) since the dough doesnt adhere to the cloth at all. You have to make sure the cloth and the pin cover are adequately but not overly floured for this to work properly. I have an easier time doing it this way than folding the dough into fourths - Im no expert.
Don't over-mix. I personally wouldn't use a food processor, but I wouldn't know if that over-mixes or warms your dough too much.
If you do it quickly by hand you can tell just how much water it needs to ball up... not to little or it will crumble, just enough to be pliable, not too much or it'll be sticky.
Make sure you let it rest in the fridge too. The gluten needs to relax.
What kind of dough are you making?
The parchment paper mentioned above is particularly helpful for sticky high-butter doughs.
Parchment paper is my answer to everything. I use parchment instead of wax because of the extra width.
I lightly flour the parchment. I roll out the dough about half way and then make sure I can unstick it with a large spatula and flour underneath. Then I roll it out completely.
Then you carefully flip the whole thing over in your hand, and position the crust perfectly over your pan. You can move it around because the crust is still lightly stuck to the paper.
Once it is arranged you slowly begin peeling back the paper. Pull at a sharp angle backwards, being aware of keeping the paper straight and any sticky spots. If you come across some sticky spots, flour your fingertips and the spot and gently unstick it.
This works perfectly as long as you keep the dough cool and work fast. I will never try another method again.