SR-225: You obviously enjoy the SR-60... so this is obviously a shoe-in. It's probably the first Grado that has the full-flavor of the higher end models. It doesn't have any amp or power requirements and responds well to any source really just as long as it's not overly bright.
HD600: Great can, scales well with higher end equipment, giving you more stuff to shop for if you really enjoy this hobby and shopping for various sources and amps to pair with each other. It's a neutral can, so it's not dark, with emphasis on midrange and bass like it's HD650 brother. Moreso on upper mids and treble while still giving you a meaty bottom end when you're listening to harder hitting music.
DT990: Just mushy and sloppy in presentation compared to the other two. Now I tried to like this headphone based on the fact that it was supposed to be a more exciting version of the DT-880s but they let me down a bunch. One thing that they are awesome with is movies and games just because you really do appreciate the big boomy signature for those types of things but over the long run, you probably want something that does the job the right way the first time.
ESW9: I have nothing bad to say about these. I like the ES7, but it feels like they're held back a bit. The ESW9 and 10 change this and give the mids "breathing room". For a closed can they sure can breath and give you a natural midrange and the bass retention is good and bass is precise and controlled which I like. The treble is polite so it's not ear piercing with poor recordings that tend to be bright and screechy. These are more portable cans though and they lack the soundstage and engaging-ness of the bigger cans. Also because they're closed they'll never be as airy as some music demands.
D2000: Boomy, but great. Everything about this headphone except the construction (the cups hang from tiny screws that are prone to breakages randomly). Sounds wonderful, is very open to modding such as dynamatting the interior of the cups as well as replacing the cups entirely! Also notoriously easy to recable yourself with something like Mogami or Cardas and it actually can improve the sound sometimes.
As for Vinyl, it's pretty expensive to acheive the same level of sound quality that a decent quality DAC can provide. Again some people pay the price due to their romance with vinyl and how cool it is, but DAC's really have all the glory these days since most music is digitally bought now.
Hope that helps!
It's really a cointoss between HD600, D2000 and your choice of Grado really.