10 years ago, I had a Jolida tube integrated (EL34) and Jolida tube CDP, with Silverline SR17.5 monitors.
I upgraded the integrated to SS Wells Majestic and replaced the CDP with a Sim 260D transport feeding an Aqua LaVoce S2 DAC.
Last spring, I put components on Symposium Svelte+ shelves and Rollerblock Jr's. Last fall, I upgraded my integrated to a Hegel H390. The latter was a huge step up in resolution and bass control. The Wells made the lower mids sound veiled and that veil is gone, now. The Hegel enabled the Silverlines to show, for the first time, just how good they are. It was as if I got a free speaker upgrade when I bought the Hegel. That took me completely by surprise. I don't see ever replacing the Hegel.
There have been cable upgrades along the way, as well.
My next anticipated upgrade will be replacing the Sim transport with a Jay's.
I am constrained by not having a dedicated room but all in all, I'm very satisfied with the steady improvement of the system.
At some point, I'd like to demo some higher-tier DACs but I can't afford to do so anytime soon.