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 * ⅓ 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.
So after I have the calculator I’ll be set.