I have no idea what to expect in your area....in my area different oak tree types tend to mature at different times with lots of overlap. The deer seem to like the white oak family acorns more than the reds, but I think they will eat whatever is available and in a location they feel safe. In my area Chinkapin oak seem to be ready first and then white oak and then bur oak. Northern red oak falls in there as well, but all the acorns on my place tend to fall within a window of about a month or even less. Now - that may just be my area...I don't know. Now as for how long the deer will eat them.....I think deer will eat them as long as they are available. White oak members will try to germinate in the fall. Bugs, turkey, rodents, squirrels, coons and other critters will also gobble up acorns as well. So acorns only tend to last for a short time on the ground before either something eats them or they simply deteriorate to the point of not being of interest to deer. They can simply rot if they don't germinate as well....they won't last forever.
Most folks look for that late dropping oak - as that seems to be the golden goose of deer habitat. That "gotta have it" food source in limited supply late in the year when deer are very active any way. I'm no oak expert and I am not sure just how much we can manipulate when oak trees drop their acorns. My opinion is that it would be tied to some sort of seasonal change and that even if you took an oak from my place and it dropped in mid October here.....it may drop earlier for you...being further north the seasonal changes may trigger that process sooner.....I would think. Keep in mind the oak tree is dropping a seed and as such they would be best off to drop when the conditions are best for those seeds to germinate....that is what they are trying to do. I'm not saying you can;t have an oak drop in December, but I have never seen one....at least not here. Maybe in the deep south....but not in my area. Also consider oaks "flower" and can be crops can be hindered by late frosts ad the like as well.
I'm not sure if I helped or not, but if your interested in hard mast production I would focus on species that are best suited for the location and soil types. Those trees will produce best for you and deer have been surviving in Canada long before people where trying to cater to their needs. typically speaking members of the white family will try to produce a crop every year and members of the red oak family will try to produce every two years. None of that is written in stone and like I mentioned environmental conditions can easily alter and affect the acorn crop production from one year to the next. As such I would suggest a mixture of both red and white family members to try to avoid a total crop failure. And like I said plant the species native to your area on the soils best suitable for that species. Forcing a red oak to grow where a re oak doesn't want to grow is almost as frustrating as not having one there at all.