Curious .. What is the compared price of your tt vs spkrs

My analogue front end is more than three times more expensive than speakers, cables not included. Next upgrade would be the amp. There is still some room for improving the speakers' performance. People often upgrade speakers too quickly.

Spending as much on a cartridge as on speakers would not be my approach, that's for sure.
Anyway, room first is the best approach, I guess. And the most expensive one.

I don't have a formula but I have a few rules that I try to follow.
Analogue front end should be very strong or all will be for nothing. I believe that the table itself is the most important part of it, then the arm, then the phono and then the cartridge. Good $350 MM cartridge sounds excellent in $1500 arm and $4000 table through $1500 phono. That's what I have. One day I will upgrade the catridge and the phono, preferably at the same time and preferable to something about three times more expensive.
The speakers. I keep them for a very long time, 15-20 years, so they must be good. I don't think that there is anything under $10k that I would really like to upgrade to, so for now I keep my 17 year old speakers that used to cost $1500 new.
I buy everything used except cartridges.
So yes, as you said, whatever sounds great, taking the cost into consideration.

I just wanted to add that the $350 MM cartridge that I have, it's UK price, it is, I think, at least $500 in the US.
$2k for analogue new - I don't see how it might be enough; used - I could try.

It appears that most of us agree that underperforming front end doesn't cut it, no matter how good the speakers might be. Or amps for that matter. 

Yeah, first things you do are room acoustics and wall current.
Oleschool, I once heard Paco de Lucia perform in a great concert hall playing incredible custom Conde flamenco guitar. Now that was a sound I will never forget, not to mention the music.

It's the same everywhere, there are many excellent people but some are too arrogant and inconsidering, and this can become 'radioactive'.
I am having a hard time of listening to any digital after analog. 
Playing the tunes and mixing in the mountains..there is something primal and basic in it, direct contact with things within and without.

Yeah, well said.