Thank you to everyone that commented. Every bit was helpful, even the sarcasm which reminds me how we cant take this hobby too seriously.
This is why i wanted to ask, not because there would be a clear cut answer, but answers which would provide insight towards the different approaches have been applied when selecting gear.
@ghdprentice Thank you so much for taking the time to explain your journey and also the experiences you have witnessed others engage in. I wish the linear length of time wasn't such a large factor in the process/journey this takes. It really helped my overly analytical mind shift perspectives. In the world of AV, computer systems and other areas of technical engineering it is pretty straightforward to troubleshoot as long as you have the knowledge and experience to know where to look.
With HiFi, I still after years of tinkering, reading and data analysis I do not feel any more confident in my assessments.
I believe the reason for this is the school of thought or philosophies that people have towards sound. There is a huge realm of those that believe that measurements and specs are the key. Then there are those in between and others who ignore it all together. This is where i notice myself struggling because today's market forces us to shop for technology based on features and tech specs. This is method is extremely efficient and provides a pretty accurate way of determining what product is right for you. However, audio is so subjective and even to the point where you might have the best specs in the world, but it doesn't sound "good" .
I also thing it was great that @artemus_5 mentioned that i always hear is to enjoy the music. I frankly can see how it is really easy to get lost in the chase. I can say with confidence i only do it for the music. I only stream as a passive listener for background music. Then i purchase media for critical/active listening enjoyment.
@samadhana I agree, and this was something that happened to me a few years ago where i built a system after trying several pre-amps and sources and was so disappointed by the results I quit listening to it. That was a really dark time for me because I really enjoy music so much, that the fact that the gear ( around $8k) was so awful to me i couldn't touch it and eventually sold it all.
@jjss49 the ripple effect is exactly what is so daunting. It really could be the most disruptive event, to me, in this entire process. But thanks for the suggestion on the LS50's. I have considered it as a really easy no brainier path. I was originally going to buy them, but my local dealer had these on closeout and the deal was too good to pass. At the same time I am concerned that the LS50's aren't enough of an "upgrade" to make it worth while. I know the LS50's are amazing for the money and have tons of reviews and i forsure would notice the difference. Which just makes me then start wondering if something like Harbeth p3, Sonus Faber's, Kef R3 Warfedale linton, Focal Chora, and so on... would be more of a "future proof" options.
@inna When you are saying you think you are close to the limits on the speakers. Are you sensing that because you aren't seeing a similar change to sound as you had seen in the past with prior gear changes? Or is more because its the "oldest" component in the system and therefor seams to be the logical place to start?
@mapman The idea of having extra gear is something i was interested in as well. I really avoid having gear laying around that isnt being used. At the same time i absolutely see the point and use this technique in diagnosing misbehaving computers in the office regularly. At the same time, in the world of separates i find it overwhelming to even begin to consider how to know what pairs well with what. Not to mention maybe you change your speakers and the gear doesn't play nice with it. Then at what point does someone give up on swapping gear or give up on the speakers?
