The $6k loss already exists whether or not you "realize" it.
Here's how I picture your situation.
10/2018
Debt: $27,000
Asset: Car = $27,000
11/2018
Debt: $27,000
Asset: Car = $24,000 (probably)
1/2020
Debt: $11,500
Asset: Car = $21,500
Net worth: $10,000
(If you buy Honda)
2/2020
Debt: $0
Asset: Car = $9500
Cash: $500
Net worth: $10,000
Overall the $266 payment is largely irrelevant unless you're living paycheck to paycheck (does not sound like, great!)
So the bigger question is how much of that payment is interest, how much more the Tiguan will depreciate between now and when you finally sell it, if it costs more to insure, fuel or maintain. Overall a lot of variables there. Compared to the Pilot, you'll certainly realize more depreciation with the Tiguan. For now, probably less maintenance, though in my experience VW end up being much more expensive to maintain later in life. You'll also lose a bit in transaction costs making the switch.
I don't think there's a 100% guaranteed right answer here, but just given what I know of Honda and VW, you'll probably easily get 100k with minimal maintenance out of the Honda, with options to greatly reduce your insurance once the value of the Honda falls within your comfort zone for self-insuring. If you hang onto the VW, you might start having problems once it hits high mileage, and the depreciation realized at that point will be pretty high.