That's what I'm getting at clumsily, unfortunately. I'm of a mind that my live oak could probably get by in-ground here in Zone 7 in an optimal full sun site that is sheltered from the North wind.
In a container, it probably would fade and die after six or seven winters--less if there's early deep freezes and the tree is still active. Keeping live oak above the Mason Dixon can be done, but it depends on what you're willing to invest to do it. FWIW, my live oak is one of the most responsive bonsai subjects I have. It's tough as nails other than the winter sensitivity (and it does snow in its native range). It can take full summer sun all day. It backbuds reliably and vigorously for the most part when hard pruned. It pushes roots like mad (it outgrew its original container) and no real pest issues (other than gall wasps in the summer which are easily removed).
If you want to provide substantial shelter for the trees you have, your live oaks will probably behave similarly. It boils down to what you're willing to put up with.