The plastic wrap seemed to constrain the dough if I didn’t “unstick” it frequently
For rolling the dough, I flour the top and bottom of the dough with Wondra, brushing any excesss off the edges and re-applying to the center as needed to prevent sticking. You do want to use flour to prevent sticking, but keep it to a minimum. You may find it easier to use plastic wrap only on the bottom, but will still need to use flour and to unstick the dough from the wrap (because it will constrain it, as you noticed!)
I also flipped hte dough frequently, which I have since learned on a YouTube video, you’re not supposed to do.
I don’t see any problem at all with flipping the dough, when you roll puff pastry or croissant you are definitely supposed to flip to keep the edges and layers even. Just don’t try it when it’s fully rolled out and thin, because it will break easily.
On the YouTube videos, everyone’s dough just flattens right out. How does this happen if the dough is cold?
Sounds like your dough was a bit too cool. It should be warm enough to flatten out- probably around 65F, maybe a little cooler to start. The trick is to keep it at 65F for the whole time you are rolling so that you don’t risk warming the butter enough to melt the flakes into the surrounding dough. I usually put a few cold things on the counter (including the dough disc) to chill it while the dough is warming.
If your kitchen is warm, put a sheet pan in the refrigerator to chill before rolling so that at any point in the process you can transfer the dough to the fridge if it seems to be getting too warm. I also put the pie pan in the fridge to chill, as the dough is often getting pretty warm by the end of the rolling process and placing it in a cold pan gives a few extra minutes to fuss with a border.
Rolling when the counter and kitchen are cool (say 65-67F) is ideal because then you’re not fighting the dough’s natural tendency to come to room temp and you can relax.
Does parchment work better than plastic wrap?
No. Parchment’s non-stick qualities don’t kick in until you heat past a certain temp- forget the temp- but it’s no help whatsoever for room temp stuff.
I only have a rolling pin with handles on the end—no marble, no pastry mat, no rolling pin sleeve (and I don’t really want to buy anything).
I don’t use any of that. But I do chill the counter by putting cold things on it.
Do you flour often? How much is a good amount to use for a single crust over the entire rolling process?
I never measured. But basically you add whatever is needed as often as needed to prevent sticking. This usually means rolling the dough anywhere from 4-6 times, then stopping to flour both the underside and the top, then continuing. It needs more at the beginning and less as you get near the end. I like Wondra because the shaker top is easy to dispense a thin, even film.