I wouldn't use oak until the secondary, but otherwise it seems like your plan would work fine.
At "age until dry", though you've left out some important things to remember. First, it'll go dry in just a few days after you put it in secondary. But it's important to rack every 45-60 days as long as you have lees forming (sediment) or when you get lees 1/4" thick. Rack to a new carboy, top up, and airlock. Once the one is clear, and no longer dropping any lees at all after at least 60 days, you can add your bourbon or whatever. You shouldn't need to degas. A well-made wine should naturally degas on its own with enough time.
I've had ONE batch in 20 years that needed to be degas. Kit wines need to be degassed because they are rushed to the bottle. But since you'll be racking when you need to, the wine should degas on its own.
I use campden tablets (one crushed, per gallon, dissolved in some boiling water), at every other racking to help protect the wine (it's an antioxidant as well as a preservative).