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I wouldn't be too worried about the Echo...as long as the transmission shifts into overdrive normally once it is fully warmed up, then it is just the cold weather that is causing the slow shifting.
I wouldn't be worried about the VW either, the transmission is electronically controled and will not allow down shifts, even forced ones, until certain speeds. This is normal.
I've been "Hypermilling/Coasting" my automatic transmission for more than a year now, if done correctly, there is no reason it would accelerate wear.
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