Ah the best money.
So best meaning whatever the value, whatever the item or event maybe even life altering.
For me, the F20 MPMan mp3 player, 1998. First commercial device, Eiger the manufacturer. Couple that with Napster and ALL that wonderful music much of which I had forgotten. The sheer joy of it overrode all the issues of modem speed downloads, and futzing with a parallel port interface to put music on the 64MB Smart Card, yes 64MB.
But then there was also Leah the Blown Gasket Girl - pretty sure I covered her mortgage for the few years I saw her regularly.