Easy answer first - I prefer the Olfa self-healing green mats. They last a long time and yes, flip them over when you wear out side one.
As to cutters, I would also recommend you go to a store; show; friend and touch and feel. I bought my traditional Olfa cutter ages ago and it's just fine. Perhaps because it's all I've known. I probably got a deal at the time and got the 28mm; 45mm and 60mm. I really only use the 45. I don't cut many layers at a time because I've never managed to accurately cut more than 2 at a time...even with the 60mm blade. Even around templates I prefer the 45 - especially with the rotating mat!
I don't use a glove when cutting but am almost religious when using mine that I retract the blade. It truly is a 'must do' safety measure when using a rotary cutter. So far I've had more nicks on my fingers from plain old scissors than rotary cutters. Fingers crossed it stays that way!