I've had both, and I've found the cat allowed outside was the one that was much more tolerable and capable of...well, just about everything. The one I owned a couple of years ago had originally been a barn cat, and she'd been amazing and better than a guard dog. She lived for 19 years.
The cat I own now is only just now, at 7 years old, becoming more self sufficient, and that's because I'm now letting him outside and trying to teach him how to BE a cat and how to hunt. xD He's so pathetic at it, I swear! Yeah, he's still needy, but that's just his personality.
I let him outside only for a couple minutes at a time, which honestly I think is all he wants (especially right now while it's cold), but I keep him inside for the most part just to lessen fleas.
He was born in a mall pet store and brought home by my cousin originally, who had bought him for her daughter. And yes, even as a kitten, he "missed" going outside. Being a vocal cat he would, even back then, sit in the window and cry for hours. Letting him outside to sit and smell on the porch for 10 minutes calms him down better than anything else. xD
It really is preference, but most of the preference I think has to do with fleas.