Over the past year I've upgraded quite often because it had been about 20 years since I upgraded before that (high school). It wasnt so much upgrading as it was exploring how things sound differently. Some were upgrades, some were side-grades. Right now I feel like I'm just fine tuning, but unfortunately it's the fine tuning that can get expensive and become the proverbial search for the grail.
I think the trick is to find a sound you like and play within that realm. For example, if you like the "tube" sound, as if there was one, you can experiment/upgrade with different types of tubes or brands. Once you find a sound you like -- dynamic, romantic, warm, detailed, whatever -- don't try to upgrade too much beyond that because you may lose it. Some components just click into place like the wheels in a slot machine and you'll keep them for a long time, or at least you should try to resist the urge to replace them.
Also, if you think you might upgrade fairly soon you should consider stretching your budget and going the next step up. This can sometimes save you worry and money.
And don't forget tweaks and room placement. These can really make or break how you like your system, whatever it is at the time.
I think the trick is to find a sound you like and play within that realm. For example, if you like the "tube" sound, as if there was one, you can experiment/upgrade with different types of tubes or brands. Once you find a sound you like -- dynamic, romantic, warm, detailed, whatever -- don't try to upgrade too much beyond that because you may lose it. Some components just click into place like the wheels in a slot machine and you'll keep them for a long time, or at least you should try to resist the urge to replace them.
Also, if you think you might upgrade fairly soon you should consider stretching your budget and going the next step up. This can sometimes save you worry and money.
And don't forget tweaks and room placement. These can really make or break how you like your system, whatever it is at the time.