12 Live oaks will take up A LOT of space!! Do you have more than an acre or two of land? They keep their leaves all year round. Occasionally they will drop older leaves, but not all at once. The leaves actually will drop in the spring just as a new batch of leaves begin to emerge, all in about a two-week period....so you never really go w/o leaves.

Here is a group of large live oaks...see if you have that much space before you take all of them. Good luck! I'm not an expert on planting them, but like most trees I doubt you could go wrong planting them in the Fall.

Here is a link that might be useful: {{gwi:346610}}

Ten to 12 foot live oaks will transplant fine if you use a tree spade to do the work. However, most other ways of digging them up will be stressful on them. The bigger the root ball, the better. November to March is best. Late April might be pushing it in hot Florida, but a tree spade and some careful watering could make it a snap.

But live oaks are tough, and can even come back from the roots if everything above ground dies. But better luck is usually had with transplanting smaller trees.

JQPublic is right. Live oaks need alot of room, their spreading limbs reach much farther than other trees. They can look wonderful all crowded together when young but will go into decline eventually and look kinda ratty.

But that's a hundred years away.

I for one don't want to leave a garden that dies soon after me.

I can tell you live oaks that size are hard to transplant by hand digging. The roots really spread and go deep. You will likely not be able to keep enough root to manually move them. Like vancleaveterry said, you will need a professional tree miving / tree-spade service. You will not be able to dig, lift, or plant them by yourself!