You won't have Murray AND Fluery by the start of next season. Either trade Fluery now or lose Murray in the expansion draft.

I assume he means that this will occur in the offseason before expansion. Simon would have to emerge as one of the top forward prospects in hockey for this value to be close (he is a very good prospect but way too under the radar to attract that kind of trade value) and even then the Pens still might need to add a bit more. But I do like your thought process of packaging Fleury with other assets to get a better asset, rather than just see what they can get for him alone.

Would the Pens really want to go with Murray and Condon as their duo next year?

Condon was baptized by fire last year having to step in as the starter for a guy who was the most important player on a subpar team, and he took his lumps, but had a number of stretches where he looked pretty solid overall. Who knows how long the Pens ultimately decide to keep him around but I think he'd be just fine in a backup role behind Murray at least until they feel Jarry is ready for NHL starts (which he has a ways to go before that)