Yes, let's talk him into redoing them.
Curtis, when was this suggested or asked of him?
Songs that he recorded in the 50s and performed live in the 70s are great to hear, but I don't think recording them again in the studio would have been a great idea. Obviously, if he had done them again, I'd sure like to hear them, but IMO re-releasing the original hits on albums in the 70s was enough.
Was it after he showed resistance to the idea that the Legendary Performer series started, and was that their original intent for those albums--re-recordings?
Considering how well they sold, I'd say they did the right thing. Not only that, but if he had actually re-recorded them, that would seem to me even more of an acknowedgement than the re-releases were that he was an artist of the past (not to say that is my opinion).
Additionally, the remakes would naturally have been compared to the originals and even if they had surpassed the prior works in quality, which we certainly should not assume, there would be a lot of people who would always say the original recordings were the best. So why risk having them fail in that respect...why mess with success?
Again, while I personally would have loved to have heard them (but not in place of anything else he recorded in the 70s), it seems to me it would not have been a wise move on his part.
Think of the remake of Blue Suede Shoes from G.I. Blues and how most people think the two versions compare. And those were recorded just four years apart--just like Love Letters, though that remake seems pretty well received among those who recently opined here. I realize neither of those examples are probably like what you are suggesting, but I think they are worth considering.
But I'm not saying I'm right about this and I'd love to hear other opinions.