Don't turn on the oven until all the cookies are cut out and in the freezer. That'll help keep the room's temp down which is important when you're rolling out cookie dough. I like to bake the cookies frozen and cut them out frozen because they keep their shape better when baking and there's no worry about them becoming misshaped as they're transfered onto the cookie sheet.
I have a side by side refridgerator too, but here's what I've learned to do in order to use the least amount of freezer space. I picked this tip up from Lisa, The Bearfoot Baker. She recomends using the 'Flexible Cutting Mats' found at WalMart to roll out cookie dough. There's 3 to a package in red, lime green and orange. They measure 12" x 15" and they're inexpensive. Lisa wasn't necessarily trying to save freezer space, she wanted to show a great way to roll and cut out cookies. BUT, the width of those mats fit perfectly in my freezer.
Ok, back to Lisa's method, don't chill your cookie dough after you've made it. Divide it into 3 equal amounts, lightly dust the mats with flour and roll out the dough with a piece of parchment paper on top to prevent it from sticking to the rolling pin. Each portion of dough will fill the cutting mat. Stack the mats putting a piece of wax paper, parchment or plastic wrap on top of each sheet of dough and put them in the freezer. When the dough is frozen, cut the cookies out, and keeping them on the mats, remove the excess dough and put cut outs back into the freezer. You can get one more mat of cookies from the remaining dough and you've only re-rolled the dough once, so you're cookies will stay tender and not toughen from having handled the dough too much.
I used to chill my dough, but three or four passes across the unchilled dough using the parchment paper has helped me speed up the process and that means more time for decorating
Regarding a rolling pin, I've read very good reviews on the Joseph Joseph rolling pin with the built in guides. I had a rolling pin and didn't want to buy another, so I use @Hani/Haniela's paint stick trick to get an even thickness to the dough. You can learn about it on her website. You can see Lisa's tutorial on rolling out cookie dough at The Bearfoot Baker
Once you get a rolling pin that you're happy with, you'll figure out what works best for you.
As far as freezer space goes "take it to the mat"! ;-)