It seems to me that the first decision you need to make is whether you want
trees in that location which have leaves during the winter or not. It may
make a considerable change to the feeling you get in your backyard and even
in the back part of your house.

Current wisdom is that due to the threat of oak wilt, one should plant new
trees which are resistant to that disease and to increase biodiversity. A
disadvantage to planting deciduous trees (other than live oaks) is that you
will have leaf drop twice a year. We have that in our font yard and over
our driveway as we have a mixture of live oak and cedar elm.

I suggest you start with one gallon plants which you have purchased or grown
yourself. Since you are willing to start small, cost of plants and
excavation will be minimal.

James Johnson

PS: You don't need to pick up acorns to prevent their sprouting. Sprouting
oak trees are easily controlled by mowing with an ordinary rotary lawn
mower.