Do you have any oaks in the existing woods? If so, you might want to have a state forester advise you on removing a few trees to let your oaks get some sunlight and room to grow. Plant a temporary screen down near the road. There are several tall annual grasses available. I would plant a 15'-20' tall grass screen on the edge and then plant alternating rows of pines or white cedar for a more permanent screen. Depending on the size of the tree plantings, you would have to replant the grass screen for a few years to let the trees grow and you most likely would need to put cages on the trees or possibly a temporary fence to protect them from browsing and rubs.
In the open area at the top of the photo down to where it necks down, I would consider planting Native Warm Season Grasses. That is fairly pricey, but you are looking at a small area. For best results, you would need to terminate the existing growth and would need some equipment to prep and amend the soil. A soil test before planting anything is a great idea. The soil ph will probably need to be dealt with, but bulk lime is fairly cheap. I have about an acre of plots and I haul a couple of tons in a trailer and spread it with a shovel. Your local co-op may have equipment that you can borrow or rent at a low cost. The lower open area below the bottle neck is where I would consider a food plot. First planting I would do a white (mix Ladino and Alsike) clover with winter rye as a nurse crop. In my plots I have planted some crabapple trees and am planning on planting some persimmons. Do some research on the soft mast trees as far as pollination is concerned. All of the above is me assuming that the top of the photo is north. If I'm wrong on that, you could just reverse the NWSG and foodplot locations.
Both sides of the bottleneck would make for great stand sites allowing you to play the wind. The NWSG will make for a great bedding area with the bottleneck acting as a travel route to the foodplot. Access to the stand locations will be key so entering from the crop field edges would allow you to avoid being winded. You will also find good stand locations leaving yours woods where the deer are entering the crop fields.
Actually a really good looking spot and I like the shape of the open area. I am sure you are aware that you are looking at some labor. You won't get it all done at once and the best way is to pick out one project at a time and finish it. I had (still have) the tendency to try to do too many projects at once. Habitat management is a process and takes time. I actually enjoy the work as much as I do hunting. It's rewarding to see the results of your work. Anyway, this was just my initial thought from viewing the photo. You may have some non-native invasive species to deal with (Asian Bush Honeysuckle, Autumn Olive, Multiflora Rose...) and that is a chore in itself!