It seems to me like it shouldn't matter how often you buy the $15 items, technically. Even if you always bought $125 items and never bought $15 items, your heuristic still wouldn't be completely irrational. If you only buy $125 items, you'll only be able to buy 4% more stuff with your income, as compared to 33% more stuff if you always buy $15 items.
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?