Are there any canopy openings? If you can find a spot that is open and will remain open for years you have a decent shot at having the oak grow tall enough. Otherwise, buy a bundle (25) seedling oaks from a Spring conservation sale or mail-order company. Plant them in a number of spots where you think they might grow. Worst case scenario they do not grow, but odds are a few will take. If they all grow, you can simply remove the trees you do not want. Small oak trees are great for wildlife and don't get out of control too quickly.

White pine grow fairly well in shade, so I don't think the risk is too great in planting one. I have quite a few growing in my pine plantation under the canopy and they look pretty normal.

I'd really be interested in seeing a picture.

Here is a link that might be useful: Improved Ecosystems

Thanks for the reply! Here is the most recent photo of the northeast corner of our yard. The property line is fenced in, and you can see where we are clearing compared to the left side of the photo. Between the bush honeysuckle and the wild grape, nearly half the mature trees were taken out before we bought the house. It is thinning, but in the heat of summer, there is certainly less than 3 hours of sunlight in most spots under the canopy.

You can also see why we are looking for some evergreen cover--in winter, everything looks bare and without the brush we lose our cover privacy from neighbor views. Oaks I want to help with the soil/drainage and simply for wildlife/native.

Do you think white pine would grow in this corner behind the patio? You can currently see this year's christmas tree propped up that we were using as a "visual." Ha!

I think white pines aren't well adapted to midwest conditions to start with, then to tax them with less-than-ideal conditions might be asking for trouble. Hemlock might work better in semishady location, though the poor drainage would be a challenge for them also. I had a similar honeysuckle-choked yard which I cleared about 10yrs ago. I have had varying success with replacement understory trees. I tried some rhodies for evergreen presence, but they haven't done great (marginally hardy for me). I have a chamaecyparis obtusa Crippsi (yellowish foliage) which has done surprisingly well; it's the only evergreen I can think of doing OK. Viburnums, dogwoods, stachyurus, yellowwood are doing well. My entire lot is wooded, so I have some specialty trees (stewartia, jap maples, parrottia, etc) near the house which are doing great in wooded setting also, but they're probably not what you're looking for.

Thanks everyone for the response! I have not heard of Burnett Woods. Will definitely have to check it out this spring. I just received three new spicebush so that makes me feel like I'm on the right track! I had thought about putting in a sugar maple but the roots scared me off, thinking they might take water away from the whole?

Someone recently suggested to me to look into a small mound planting of 2-3 northern white cedar for an evergreen presence? Suggestions or thoughts on that?

I would check out cold stream farms if you want good quality trees for real cheap. Beech, sugar maple, and hemlock can handle deep shade. I would also consider the hickories as they often grow in a community with oaks. Don't forget the herbaceous layer....trilliums,wild ginger, crested iris, ferns, black cohosh, etc.

Here is a link that might be useful: Cold Stream Farms