To a degree I also think it relates to needs & wants too-personally I haven't updated since 0822r8,according to a quick check-but given my lowly late-gen socket 370/PIII based specs (& more so that I'm perfectly happy with the compatibility of the games I like to play under WinUAE), I have no reason to contstantly go for the latest & greatest.
Unless there's a specific game that you can't run under an older version of WinUAE,then you should stick with the old,after all if it ain't broke....