Other than maybe a sub, assuming you have source material to justify for both, to make the best progress, always focus on getting the lesser source to match or exceed the other in general.
Sounds like digital is the lesser currently.
One can get both to sound very close but likely never exactly the same. That's OK. When you find yourself enjoying and always looking forward to listening to the next favorite on either without concern for the sound of the format, you are done.
You may well not have to drop the entire $2000 for the first enhancement/tweak. A lot can be achieved with digital sources or subs for under $1000 Keep the funds around as best as possible so you have them if/when the next tweak is needed. Take smaller well researched but inexpensive steps rather than drop the budget in one shot and take a chance on an expensive new device that may or may not help and will depreciate considerably as soon as you buy it.
Also be sure to always work to keep the setup in th e room optimized for best performance there (sounds like you do that already) before taking the next step.
Sounds like digital is the lesser currently.
One can get both to sound very close but likely never exactly the same. That's OK. When you find yourself enjoying and always looking forward to listening to the next favorite on either without concern for the sound of the format, you are done.
You may well not have to drop the entire $2000 for the first enhancement/tweak. A lot can be achieved with digital sources or subs for under $1000 Keep the funds around as best as possible so you have them if/when the next tweak is needed. Take smaller well researched but inexpensive steps rather than drop the budget in one shot and take a chance on an expensive new device that may or may not help and will depreciate considerably as soon as you buy it.
Also be sure to always work to keep the setup in th e room optimized for best performance there (sounds like you do that already) before taking the next step.