I finally got this brewed a little over a week ago using the updates to the recipe I suggested above. All grain brew came in at about 1.079. Initial fermentation went very well and I plan to rack to a corny keg this coming weekend. I decided to go with half the supplied oak and those are soaking in 16 oz of Blanton's right now. I'm guessing that the flaked oats, flaked barley and yeast selection will likely push this into something closer to a stout. I'm hoping for a richer mouthfeel.
I have Madagascar Vanilla beans on order that should be here in a couple days.
My plan is to rack to the keg, purge O2 and let it bulk age for another month or 6 weeks. In September I'll add the oak/vanilla/bourbon mix and repurge the O2. I can then draw off a sample once every couple weeks but I plan to leave it on the oak until November or so. Whenever I deem it's ready, I'll just stick the keg into my kegerator, do a force carb and bottle from the keg.
I haven't tried a sample yet, so I'm really excited to rack to the secondary, taste and get a gravity reading.
All the above timelines are subject to change based on samples. I really want to give at least two weeks secondary before I add the bourbon mixture. Other than that, everything else will be based on how it seems to be progressing.