Shaddow has been our kitty for about 3 years (his age, too), and while he was a feral cat for a little bit, the night we brought him home he calmed down immediately. I woke up and found him sleeping on me ('; Since then, he's been my baby.
Anyways, our old kitty eats soft food, so it should be no problem to get Shaddow to eat soft, too. In fact, now that I think about it, when he was sick he was fed soft food, and he used the litter box then... O.o He was raised on soft food, so actually prefers it.
The current litterboxes are in a very tucked away corner and in the basement where no one goes except for the cats, so I'm sure it's not privacy that he's lacking.
And last of all, we're going to set up a litterbox where he "goes" the most with some shredded newspaper, to see if he prefers that.
Thanks for all of the help (: I'm trying to get up the guts to euth Vulcan...