I took a somewhat similar path; started off with a HD800, then LCD-2, finally -3 (all with a variety of rather good amps), while looking at SR-009 all along. I suspected one was going to be in my future, but for whatever reasons I kept postponing it, thinking that for the little listening I will be doing I might not want to spend all that money.
Then one day I finally bit the bullet and just went with it. I guess what I am trying to say is that I've spent a lot of time tweaking, changing, upgrading - all to the inevitable end. If you think you will end up with a SR-009, and have the financial means to pull it off, there might be better ways for you to spend your time than monkeying around with intermediate setups.