RE: So you think you know trees ?
If you have some land you are going to have for a long period of time I would suggest some of the smaller oak species such as sawtooth oaks or shingle oaks. They produce acorns quickly and abundantly. The sawtooth is probably a better choice as they are known for rapid growth and wildlife love the acorns. The shingle is slower and is a red oak so the acorns are more bitter but they tend to fall later and once the cold hits the animals don't mind the taste as much, once they start producing they seem to produce heavy crops more frequently than many kinds of white oaks. Oaks are sometimes hard to id because there are actually a lot more than people think. We tend to think of White, Red, Water, etc but realistically each main type has many sub species and in old stands of woods there are often hybrid species.
We planted close to fifty shinglesin the past couple ofyears and several sawtooths as well. Most won't make it but they were planted from acorns so it really didn't cost anything and the few that start to thrive we fence and fertilize. You can get whips of most oaks for pretty cheap not to mention crabapples, mulberry, pears, wild grapes, blackberries, etc. The trees are a long term goal but luckily we own the land so hopefully it will pay off in 10 years or so but the berries, grapes, and any other low level shrub/browse will develop quickly and almost immediately become beneficial.
The dept of game in your area probably has lots of info on food sources that are relatively easy to plant/maintain. I knowin VA sometimes you can even get free seed kits and samples they can even tell you how to get incontact witha bioligist who will look at your area and offer suggestions, tips, etc. at no cost to you. Be sure to ask about fall/winter plants & planting. Sorry so long.