But if the time to drive across town is worth more than $5 in the $125 case, it's worth more than $5 in the $15 case, and forming that habit loses big. (Unless driving across town once allows you to save on more than one item, but that completely breaks the example.)
Other than cognitive cost, I don't see any reason to speak in terms of habits rather than case-by-case judgments here.
In the car case, you know the cost of walking away is very high; this screens off the informational value of the price.
From Tversky and Khaneman's "The Framing of Decisions and the Psychology of Choice" (Science, Vol. 211, No. 4481, 1981):
This one's a killer. Money is supposed to be fungible, but these observations really highlight how difficult it is to really behave as if you believed that. So, aspiring rationalists, how might we combat this in ourselves? Maybe it would help to consciously convert between money and time: if you value your time at 25 $/hr, then the cost of a twenty-minute drive is 25 $/hr * (1/3) hr = $8.33 > $5, so you buy the calculator in front of you in either case. So this heuristic at least takes care of the calculator problem, although I would guess it fails miserably in other contexts, I currently know not which.
Another takeaway lesson is to ignore advertisements boasting that a product is currently such-and-such percent off. We don't care about the percentage! How many minutes are you saving?