When I roll it 1/8" thick or thinner; maybe my fondant is too dry and rolling on cs or ps is drying it out more. Please give me your best tips on what you roll it on; how/what you lay it on; how do you store it to keep it pliable to bend without cracking? Thanks!

I use store bought fondant and use crisco to prevent it from drying out. You can store fondant cut outs between saran wrap if you put a light layer of crisco on them. I haven't stored for more than a few hours though.

Place them in a zip lock bag, seal and place a damp (not wet) cloth on top if you are going to use them in a few hours.
You can also place them in the fridge or freezer while in the bag. Just make sure that they are in a single layer or they will stick together.

I haven't been able to figure out a way to successfully store fondant cut-outs overnight. I've tried several different methods (saran wrap, tupperware, etc) and they are just too dry. Now I just complete the decorations when I'm finishing the cake. I try to do anything that needs to dry hard several days in advance to give me a little more time so I have more time to work on the things that I need to stay pliable. I'm curious if anyone else has managed to successfully do the cut-outs in advance.

Thanks everyone. This is important for me to know because I can be a procrastinator; lately I've been handling my time management very well by doing everything in advance including making the batter ahead of time and freezing it.

Dsilvest thanks. I'm going to try both of your suggestions with some leftover fondant; time how long it takes to thaw so I can determine which works best for me.