Most of the "life" of a deciduous tree is in the roots. Unless the cause of the tree dying is a tree disease that can reside in the roots, then I would certainly try to re-grow the oak trees from a stump base. If the roots are healthy, and you prune back to only promote the best stem, then you should get phenomenal growth rates.
No great loss if you fail - it is easy to cut back a dying stem if you decide to finally terminate the tree.
There has been a deliberate practice (coppicing) in Europe for hundreds of years of fostering new growth from the stump and roots.
Wikipedia - Coppicing
