Did your system getting better the more money you spent or more experience you gained?

Both. I have, in the very beginning tried to minimize cost and maximize effort (gaining experience) and found I wasted more money by trying to save money… I would try going low cost and just ended up buying three intermediate components and the final one. I definitely never invest less than 2x or more on each upgraded component… I have learned that is a great way to be very disappointed. 
 

However any purchase that was not hugely researched and considered in the context of my system has not been as effective either. So, you really need both to build better and better cost effective systems.

I suspect how much time you have / money you make strongly enters the picture here as well.

I've been careful not to outspend my knowledge base.

It is both. It took me some money to determine what I like / trying to achieve. Then through reading, listening, think I had to spend less to get close to my goal.  

Great responses. I think l got to a point where I tried to learn as much as possible then I ramped the spending up more. I was extremely careful with the last 2 purchases. The Infigo method 4 & 6.  But I got to demo first and that was the key. Trying before I buy.  I was able to go amp source cables one company and it worked extremely well!  But you can’t just spend a lot of money and get it right based on cost. 

Anyone who has watching Danny Richie from GR-Research has seen first hand that spending more money on audio does NOT ALWAYS equal better performance or even better parts.

I think it’s naive to think that it does, but it is a natural inclination to think that way because often times spending more money DOES bring better performance. Having said that, there are many factors which would contribute to better sound with synergy being one, individual hearing ability as well as having a trained ear as two more, the "I got more expensive new gear so it must be better" factor being another and so may others etc, etc.

I think experience would be the far more important factor as well as knowing one’s self. Taste in sound is another important factor and so is the degree of arrogance or objectivity and open-mindedness (internally) one has to recognize when listening to gear.