The whole habitat improvement thing can quickly turn into another hobby!
When we first bought our place it was oak "poor". Lots of walnuts and hickories, just not many oaks at all, so that's been a focus. On my 80, in my back 40 deer engagement area I've planted:
Oaks; Sawtooth, Burr, Chinkapin, Nuttall, and I've cleaned up every natural growing oak I could find.
Dunstan chestnuts
Common Persimmons
Arkansas Black Apple trees with a bunch of Dolgo crab apples to pollinate.
Pear trees (2)
Paw Paws, just started this last year cause my wife wants them..
I also plant 2 food plots and have a mineral site.
IMHO Common Persimmons are one of the best, IF you're a rifle hunter. I've always had a bunch of them, but not where I needed them to hunt. So I started planting them further back in order to hunt near them. The commons hold their fruit longer and will drop slowly pretty much from late OCT through DEC here in KS. Turkey's, deer, and coyotes love them. have to be careful with them as they have two sexes and you need both to pollinate. Once they get going, holy cow due they produce fruit!
As far as trees go, it's a long term project, some oaks won't even start producing for 10+ years (bur Oak 30+ years!!). I've tried to get a mix of red/white and space out their drop times. For instance, Sawtooths drop early around Sept, so may not be of much help for rifle season. White oaks get gobbled 1st, so you need some reds to get through the winter. My Chestnuts 3 year olds when I planted them are now going on 10 years and a couple are just starting to produce.
For a couple years I even stratified acorns and persimmons in my fridge during the winter, then planted them in pots through the spring/summer, and transplanted in the fall. In one year I put down close to 70 seedlings and started trees. Now I'll catch the fall sales and just grab a couple oaks and plant them where I've got a gap.
Arkansas black are a late ripening apple, so they'll be dropping in late OCT/NOV. Pears are cool because they produce a lot and are pretty low maintenance.
Oaks in tree tubes:
My 1st Chestnut:
older persimmons: