@baylinor +1
Bluethinker - I tried to look at your virtual system but it is blank. That might help with getting advice here from those way more knowledgeable than myself.
I learned the hard way that the wrong tube amp paired with a non-tube friendly speaker (or vice-versa) can be an expensive mistake.
Be wary of the cable-chase - you need decent cables to progress, but significant gains can be made without spending silly money on the right used cable (safest bet in used audio IMO, pretty hard to destroy cables). As a recent example (only), a used Voodoo power cable and Acoustic Zen speaker cables bested all previous purchases. Both examples were from recommendations by fellow AG members. (thank you!)
Lastly, use good reference material - tracks you know well, and don't rely on a quick a/b test. Take time - 3 days later you might just turn your head and think wow, never heard that before, and I like it...that's a good indication you are going in the right direction.