I often bought used, traded, flipped stuff but I am at a point where my kids are grown and my bills are low. That said , about two years ago I started a major upgrade.
I spent more than i originally budgeted , but I am at the point where it sounds so good and I get so much enjoyment that it's immaterial.
Biggest and best purchase was a 300b amp by Toolshed Amps. I saved for over a year for that one. Worth every penny. It is a fantastic sounding amp. The tone and transparency is addictive. Build quality is over the top, heirloom quality. It was a little more than my ceiling of $5000. That ceiling was broken when i spec'd Amorphous OPT and a few other options . It is so good I am having Matt from Toolshed build me it's companion DHT preamp.
I expect this to be my last amp / preamp combo so I'm already saving money by hopping off the amplifier merry go round.