First, I only base my decisions on the sound qualities. Never the technology used. I have had components basses on ESS DAC chips and they have sounded everything from terrible to great. It isn’t the technology, it is the implementation that matters. The designer has to choose the design, technology, components, material… etc. I pay absolutely no attention to the technology.
I never have a stable. I always trade up, and never less than 2x in cost from my last component because if well chosen it will sound much better than the last. Otherwise you trade one set of weaknesses (and strengths) for another. Trading up, all aspects get better.
I read professional reviews and listen to everything I can, including lots of live acoustic music. This approach has led me step by step moving towards better and better systems.
Now, being retired and having the time to really enjoy the system I have built over fifty years is really rewarding! The only larger investment I have made is the house in which it sits… which by luck has the best audio space I have heard (better to be lucky than good).