I laminate mine every week, and really have little trouble -- given that I let it rest for a couple minutes when it gets hard to roll. Here's what I do:
I take half the dough recipe from above in this topic, which for me will make a 12-inch pizza with some leftovers for crackers.
I roll it out on my Silestone countertop and use very little bench flour -- just a dusting to keep it from sticking too much when it really gets rolled out. I use one of those tapered rolling pins and roll it into about a 12-inch square. Then I cut it into four 6-inch squares and spritz three of them with a little olive oil from my olive oil mister. Then I stack these with the un-sprayed one on top and start rolling it out.
I can usually roll this back out to about 9x9 inches before it starts fighting back. So I walk away and do some other prep for a few minutes, then come back and continue rolling. Using the tapered pin, I'm able to roll the stacked square out to about 14 inches in diameter. It ends up about 1/16 - 3/32" thick. I then dock it and put it into the cutter pan, and trim it, then into a 500F oven to parbake for 5 minutes.
It does get a bit tough to roll at a couple of points but letting it sit for a couple minutes lets me resume the rolling. The laminated result I get is worth every bit of effort.