Aside from the flipping of the window scrolling mechanics, most buyers seem to think Lion, the latest edition of the Mac operating system, is worth the thirty bucks or so it costs to upgrade. But one customer isn’t quite so happy having paid nearly $4,000.

Macrumors reader John Christman bought the upgrade last week, expecting to pay a total of $31.79 including sales tax via his PayPal account. After some problems with the upgrade he opted for a fresh install. He then fired up iTunes and took advantage of a feature that automatically reinstalls all the apps you’ve previously purchased or downloaded without charge.

Unfortunately when the first app downloaded, his PayPal account was charged $31.79. When the second app downloaded, his PayPal account was charged $31.79. When the third app was downloaded… well, you get the picture.

In total, the automatic reinstallation covered 116 apps. To make things even worse, a few downloads screwed up and were carried out again, attracting further $31.79 charges. By the time the process was done, he’d been charged 121 times, totalling $3,878.40.

Christman complained to both Apple and PayPal and then formally filed a dispute with PayPal. At last word his account listed every bogus transactions as reversed and refunded, backdated to the day of purchase, but the money itself hasn’t shown up, which Christman says doesn’t bode well for the mortgage payment that’s due this week.

It appears the problem is fairly widespread, with numerous cases of multiple charges, though few were quite as unlucky as Christman. One customer says he has been told by PayPal that despite the refund being granted, the procedure is that the full amount of the bogus charges will be taken from his bank balance but then immediately credited towards his PayPal account, allowing him to return the money to his bank account. Of course, that doesn’t help him with the resulting bank overdraft fees.