I think with all of this there's always a few points that will always be "the best" way to go about it.
- Buy the best you can afford
- Price should be based on usage
- Noticeable upgrades, will usually cost you double of what you currently have. (Baring that diamond in the rough Bang for your buck unit...they are out there)
To elaborate a bit, CD's have become a viable format due to scarcity and cost of certain vinyl pressings. With that said, I wanted the best I could muster without going overboard because the reality is that I'm still most likely to drop an album on my TT than load up a CD. So I set a budget that I felt could get me something decent ($500ish). Settled on the Audiolab 6000CDT, because I still like the option of swapping out the DAC instead of the entire unit, then added a simple Schiit Multibit to it and it was pretty dang good.............for my usage.
I'll also always back the logic of not passing on deals and or opportunities, IF, they still fall within your budget. The Denafrips Ares II pretty much solidified the CD part of my system at a price I was ok with, it just kind of popped up, was able to pick it up for $570 used and the world is a wonderful place.
There is always "better", but you can't just keep spending your time and money chasing in this hobby. I ran through A LOT of gear, but with a purpose, to find my sweet spot at my cost. Don't get too frazzled in the gear, gear now a days is leaps an bounds beyond where it was, you don't have to spend a lot to have a good system, regardless of the format.
In the end, don't spend too much on the piece of the chain you might not use as much