Boy, if we could get either of those deals from the Tigers or Rangers this offseason, I think you HAVE to move Woody. As has already been outlined in this thread, you have little to no chance at signing either Woody or Burnes long term, so I think it's imperative that we move one of them this offseason to get as much trade value as we possibly can from them. Yes, it would hurt to lose one of our "big two" arms, but as we all know - we do have good SP depth right now with our major league staff.
We could still roll out a rotation next year of Burnes, Freddy, Lauer, Houser and Ashby - with Small in the role that Ashby has been in this year.
Then, if you make that deal with the Rangers, you'd potentially have Leiter waiting in the wings to jump into one of those rotation spots. Jobe (deal with Tigers) would be further away from being a big league pitcher, so making that trade with them would scare me just a bit more. But, if DS and Co. like Jobe's upside better than Leiter - then maybe that is the better route to take?
This still seems like a lot though to me for either the Tigers and Rangers to give up from their farm system.