I think the whole "old car" with a "new motor" crammed into it fad has gotten stale. Nothing about it is really unique anymore. And unless you're really sinking a to of money into the interior, its not going to be a comfortable as a newer car....so you're basically spending what could be a ton of money to make an old turd a new car.
It's stale because it's the only way to go with an older cruiser. Unless you have a rare numbers matching car or a desirable power train combo, there is zero reason to not upgrade to a newer power train. That's you think it's stale. The wow factory is gone I admit that. It's still really cool.
No a 3rd gen will never be as comfortable as a ZL1. It still would be half the price. Also I'm not daily driving the car. It all depends what experience you want when you drive the car though. That's my dilemma. Do I want the older, nostalgic feel or do I basically want a daily driver will more power.