MrBob, you do a great Puddleglum!
I think that in the character of Puddleglum, Lewis did a superb job of displaying the difference between temperament, which is a personality characteristic, and deeper virtues such as faith and fortitude. Puddleglum, who was modeled after Lewis' gardener, definitely had a pessimistic temperament, but was a model of faith. Even though delivered in his typical glum and dour style, his defiant denunciation of the Emerald Witch's seductive reductionism was as ringing a declaration of faith as you'll ever hear.
It seems to me that our time is far more enamored of superficialities like temperament than it is of deeper, more meaningful personality traits. We'll prefer the company of a nihilist who is an interesting conversationalist and fun party companion to that of a fussy, fidgety old man who has lived a serious faith for years. Puddleglum helps us to see that it's the deep traits that matter.
Here's what I think: remember that the main reason for Puddleglum's repeated gloomy outlooks was that he wanted people to see reality as it was. He didn't want anyone entertaining any illusions about their condition or looking through any rose-colored glasses. Most of what he said was intended to get people to face reality squarely.
In the New Narnia, he would have been surrounded by unadorned, undisguised reality - in fact, a "more real" reality than he'd known in the Old Narnia. Furthermore, everyone would be seeing it clearly and without illusion. While I think he might have felt "out of a job" at first, I think eventually he would have warmed to the idea that he no longer had to encourage people to grapple with reality - they were doing that. I think he would be one of the more serious and profound residents of New Narnia, but I doubt he'd be downcast or joyless.
