Like Diamond Dog, I have no interest in incremental changes. Everything I've bought since my first system was a pretty big upgrade. I guess they were all equal steps up...
Went from an NAD 304/Playstation 1/White Van speakers (seriously) while I was an undergrad. Upgraded the CDP to an NAD 523. Very big upgrade, even through some of the worst speakers you could imagine.
Then bought PSB Century 100 (I think) speakers. Huge upgrade. Live with that sysyem for several years, until I got my first real job after grad school.
Bought an NAD 320BEE to replace the 304. I guess this was the smallest change ever, yet it was easily worth the money. Upgraded to PSB Image T55s, and again, very big improvement.
After a few pay raises, I put together my system as it almost is today...
Bryston B60, Rega Apollo, Pro-Ject 1Xpression w/ Speedbox, acrylic platter, and Dynavector 10x5.
Replaced the Apollo with an Apple TV gen 1 and Rega DAC. Big upgrade yet again.
In the spirit of this thread...
The B60 is truly the star of the show. It's easily shown the differences of everything around it. Speaker upgrades, source and cartridge upgrades, cable upgrades, even tweaks.
The Apple TV changed my system for the better from an ergonomic/convenience standpoint far more than any other piece. No more searching for CDs, changing CDs after 1 or 2 songs, and so on. I've got my entire collection at my fingertips through my iPhone as a remote. Best thing for my system in a very long time. It's a paradigm shift. Won't go back to a CDP ever again.
The biggest enjoyment piece is my turntable. There's just something about cleaning an album, sitting down with a huge cover and liner notes in your hand, relaxing and enjoying some vinyl. I've had it packed up for about a year and a half now due to a move and my beautiful 15 month old daughter, but it'll be back out soon.
My Rega DAC was a big improvement on my temporary Theta Cobalt DAC. The Theta was excellent, but the Rega just trounces it.
Cables have had the least impact on my system. There's definitely differences, but I liken them to that last dash of seasoning on food. Sometimes a pinch of salt brings it all together, and that's how I view cables. I don't get these jaw dropping results magazines and people on forums talk about. Some people on Audiogon would have you believe cables are just as important snd make just as much of a difference sonically than components do. Never heard a cable do that much.
Sorry for the long post.