Which route would you go and why? TIA...

Dakota only if you're worried about resale and Penrod if you want to be able to pick and choose your components to your exact specs

You don't mention what kind of rifle but for a synthetic stock rifle I would go with Mark Penrod. I've never had a rifle built by Penrod but one of these years....
For one you could get the Mcmillan stock of your choice including the Echol's stock and they have checkering...the Dakota doesn't. I like the Win. trigger better than the Dakota 97...simpler. Blackburn bottom metal..on the Penrod custom...if you wish, checkered straight drop bolt, paint color etc. In other words , built just the way you want it...barrel contour etc.

Actually I went with WF Hein and Hill Country Rifles for two custom rifles being built now for all of the above reasons but I have a pre 64 .338 action I would love to send to Mark.