Replacing trees

I have a one acre property with about 10 large oak trees. Probably 80 to 100 yrs old.

I want to plant new oaks to replace these ones down the road. Some of the other oaks in our neighborhood are starting to die off, mine look healthier than most but have some dead branches here and there.

Am I able to plant an oak tree that is shaded by the older oaks to get established then grow in place of the old ones after 5 to 10 years, could be longer for these old boys too? The yard is shaded but we are still able to maintain a healthy natural lawn underneath it.

I don't want to take down any current trees but don't want to end up with a bare yard if these trees were to disappear.

Any good resources on how to properly maintain the trees on my property?

Southern Mn