When is it time to up grade?

I have been considering up grading my equipment but the question is what would the most effective and best sounding path. My ampis a Classe Ten and pre-amp is a Classe Four. I'm leaning towards replacing the pre-amp (phono-stage could be better I have a low out put Linn Trioka) but what do you say. I'm limited to about $3000 CDN. Looking forward to you thoughts.
What time is it?
when you have the money and the time. Move from ss to tubes. cartridge and speakers are probably the most colored components in your system.
One thing I would look for is a used Aesthetix Rhea phono stage. This is a very good phono. If you prefer to look for SS in that range, check out the Pass Labs Xono. I can't imagine you'd be disappointed with either.

Don't do anything foolish like dumping solid state for tubes without seriously auditioning the particular piece of gear. If tubes are the answer, your question is too vague.
When your checking account is no longer overdrawn ;~)
You mean you haven't yet?
When you are no longer emotionally "moved" by your present gear...
Whenever the "preamp deal of the century" becomes "the preamp deal of the millennium". Then, at least, I'll know.
How about some speakers?
My speakers are Castle Howards. They work well in my crowded living room.I haven't auditioned any new speakers in a long time. Are the Castles the weak link? Replacements?
When those evil upgrade gods whisper in my ears, or every week which ever comes first.