A classic one in the US would be the choice of visiting the doctors. The rich can afford to have regular checkups(or insurance) and get a sniffle checked out early. The poor can not afford to visit the doctor over minor ailments and because of this end up spending big in lost time at work and more expensive one off treatments for a serious illness they didn't nip in the bud.

But I'd have to concede that you'd be right to say it still doesn't fit the boots analogy with out some rather lax semantics around up front vs long term cost. You could also argue that any individual might get lucky/unlucky and so it's not clear cut there, but I think it would be fair to argue that in aggregate the outcome on cost is a reasonable example.