Mark
As someone who has faced similar situations, and as someone who hates to see opportunities wasted I will weigh in on this.
First, there will be some serious work turning that tree into something ready for the sawyer....de-limbing, and getting it bucked into sawlogs is a separate job, possibly complicated by the fact that that tree looks to be not all the way down...be careful if you decide to do that yourself.
Second, from what I can see there is access and space to drag the logs out to where the sawyer can set up for milling, so that looks to be doable. A 40" x 10' log will be a challenge to move without proper equipment. Three such logs will yield a fair amount of lumber to be moved, sticked, etc. The fun will go out of the process pretty quickly. Be aware that in the end you will have plenty of firewood from the limbs to deal with, and a sizeable pile of sawdust at the milling site to clean up as well.
Third, I am not sure storing the lumber under a deck is a great idea unless it had good cross circulation...most decks tend to be damp, not great for drying. In any case, preparing the "beds" for stacking is a chore in itself and does require some work and expense making a solid, level foundation for each of the piles. That might be more difficult to do under a deck unless it has good overhead clearance.
Fourth, think about how you might want the lumber/slabs cut. If you are a furniture maker and want finished 3/4" stuff in the end, I would suggest having the sawyer cut it 5/4 to allow for dimensional changes during drying and for inevitable loss of dimension when jointing and planing to that thickness. Air drying that will take about a year, thicker stuff will naturally take longer.
Fifth, If you are thinking of offsetting your expense of lumber production by selling some of it, be aware that the desirability of air dried lumber is significantly less than the kiln dried variety which commands a higher price...I am thinking that you may get less than half the retail price. That is disappointing after you have put in significant effort and expense to get the lumber to that point.
So having said all that, an attractive option would be to see if you can "sell" the logs to a sawyer who will share to lumber with you, cutting your overall expense, leaving you with less work in the long run and probably provide you with more red oak than you will ever need. I am not sure how probable that option is. Sawyers I have used charge by the hour and it has ended up costing me about 50 cents a board foot to cut...but there were two of us grunts pushing the process doing all the offbearing...pretty hard on the back but shortening the overall sawyer time.
So in the end, you will do a lot of work, and you will get your lumber for a good price, and you will have more of one species of wood than you need...by a lot.
How do I know that? see below
