Where did you sink the most cash into?

My Silverline Boleros represent about 50% of the value of my audio system, excepting my music collection of course. 

Very nice speakers, BTW. :-)

I'm old school & was always taught & truly believe to spend 50%-60% of total budget on speakers - of course back then all you needed was speakers, a receiver, turntable & cassette deck for a system.
I still believe in spending about half your budget on speakers, then amp/s, pre, phono, cartridge, cd/sacd & cables.
It has always worked for me as no matter what source you select it will be heard from your speakers.

Most of my cash is in music.
Only 10% or less in equipment.

I started collecting records as a teenager. In looking at my collection, without a doubt, the music collection would cost more than my stereo system by far. Original Blue Notes, Six-eye Columbia's, Original Contemporary's, Riversides, Roost's, Pacific Jazz ... and then there's the classical ... 

Speakers, analog, amp, digital, cables. But the system also sounded great when it was analog, amp, digital, speakers, cables. I don't really think about where a component falls dollar wise in the system.  I just buy what sounds good.  But I do think that if you like analog, you can really hear where the money went when you upgrade the front end. IMO.