I think there will always be questions about what, how, why and who were are and people willing to share their thoughts on these questions. If Progress lies in better explanations, opening up our imaginations , expanding our conceptions enabling us to see ranges of possibilities, then yes.

An un-examined life is not worth living.

No, just regurgitation.

Philosophy is the love of wisdom.
That's enough for me to want to continue on with it.

Philosophy is a large field.

Depends on how you define success. If success is "having everything figured out" then philosophy will never succeed. If it is simply providing more effective ways to understand and work with the human condition then it can be argued that it's already been at least partially successful.

Very little. Philosophy used to take into consideration the latest developments in science, but that got too difficult for philosophers in the earliest 20th century, so very little interesting or meaningful philosophy has been generated for at least 100 years.

Ethics is part of philosophy and with new technologies often come new ethical dilemmas like the self-driving car stuff. Even though the trolley-problem in itself is not new there are interesting things to work out in the details that might come up.
Most things regarding consciousness are also quite an open field, so there is still some things that science might settle one day to be speculated of by philosophers.
Also I think old ideas need to be put into modern context. Almost nobody has ever read Plato but I think there is value in considering his ideas and his impact. Political and social changes could also be more influenced by philosophy. That there is not much of that is one reason why so many people still cling to religion.
So I think that way progress could also be made. Not necessarily by producing new ideas but by being more like a historian of intellectual discourse.