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Trade in whatever one would be more practical for you to part with. Logically, it makes more sense to trade in the vehicle with higher miles and older.
Also, depends on what kinda shape both vehicles are in. If one has been coasting you more and more to keep, it would not make sense to hold on to that one imo
I personally love 2 door Tahoe's/Yukon's. I just don't think they are "daily driver" vehicles any more. If I were to buy another one, it would be a weekend driver. Just throwing it out there.