Those are great looking stacks and you are doing everything you can to get it dry. Good work!
Will it burn this winter? Yes it will. Many people do this and give it far less time than you. Will it burn efficiently? Well a good bit of heat will go up your chimney, used to burn off the extra moisture. This will require you to burn a bit more wood, and check your chimney fairly regularly. It can be done - I did it this way for years before I joined this forum. I agree with osagebow about trying to get some ash, or some other softwood that will dry faster. Mix in with the oak and it should be okay. If you have the space I would order a bit more now for future winters, or cut your own if that is a possibility. Good luck!
One last thing: Will 2 cords get you through the winter in Massachusetts?
Thanks. I am not sure how much wood I will need or go through, since this is my first time ever trying this. I currently use and will continue to use an oil boiler with cast radiators. I am in eastern Mass, 1 mile from the ocean so our temperatures are more mild than more inland areas. Also, my house is very well insulated and is only 1470 sqft. Most other people I know go through 2-4 tanks of oil but I only use one 275 gal tank per year. I calculated the btu's and 275 gal of heating oil has less btu's than 2 cords of hardwood. I will be taking this slowly, I have three small kids and may focus on evening and overnight burns until I am feeling more comfortable with the process.
As for getting wood for this winter. I have read several places that burning seasoned pine is ok for woodstoves. Is this your understanding? I often hear people say you can't burn pine in a wood stove because it has too much resin and produces excess creosote. What is your take on seasoned pine?