Your premise of retiring the Shuttle because it's '60's technology is flawed. Just because something is technologically old doesn't mean it's useless. Examples: the SR-71, U-2, B-52, the Champ, the J-3 Cub, the Hoover dam. Simply abandoning the technology because it's old doesn't make sense, particularly if it's still viable. The only way to advance future systems is to build on the past. There will always be failures with complex systems. True explorers accept that fact and keep going.
Given the complexity of something like the Shuttle, from conception to deployment often taking 20 years or more, making the technology, by your terms, obsolete at deployment. With this sort of thinking we'd never accomplish anything.
Two things are glaringly apparent to me after closely following the space program since the late '60's and reading your reasoning in this thread to abandon manned spaceflight. One, there is no substitute for human participation in spaceflight. Two, some people are so afraid of dying that they don't know how to live.