I think "a satisfying point - still some tweaking to do" pretty well sums things up for me.
I swap gear around for the fun of it, to hear what things sound like and to seek out synergies, etc... but generally I like a lot of what I hear, esp. in the main system, especially when I have the RS IIs hooked up.
SPEAKERS:
I don't know how much it might be synergy between speakers and room, or what, but I have yet to find a pair of speakers --of any type-- for sale that I think is significantly better than my RS IIs. They are so revealing that I can't listen to most of my CDs through them, but with good recordings (mostly analog) they have such a musical reality that I still get chills down my spine sometimes, even after nearly five years of listening to them. Yes, I've heard better: the IRS Vs. But that was years ago, and I have no reason to believe that there is realistically a set of those on my visible horizon. Maybe one day, further out, I'll get them, or perhaps 1bs, but I wouldn't swap my RS IIs for the Utopias, Acoustats, Magneplanars, Avante Gardes, big JBLs, vintage Altecs, Ohm Walsch, MBLs, or any other fine speakers I've heard.
What I do have a real HOPE will sound even better, in terms of speakers, is my DIY project: an open baffle line array of "Great" Heil AMTs on each side. PERHAPS supplemented with columnar Watkins woofers on each side, a la the IRS Vs. But these will, no doubt, take a couple more years to complete, as finding affordable AMTs is getting harder each year.
So am I satisfied in the meantime, with my speakers? YOU BET! I have others like the NS-1000Ms for near-field and daily background listening, which are also very fine, and a selection of other speakers (DQ, DCM, AR, etc...) to choose from for variety. Any of these I could live with and not feel frustrated, if they were all I had. They are all GOOD speakers.
I have three active crossovers to play with, and between them I'm okay; they give me sufficient flexibility. I may upgrade them one day to something superior like the Accuphase ones, but I can't hear any deterioration that bothers me with any of them.
ANALOG SOURCES:
My best turntable is, no doubt, the newest one: the Yahama GT-2000. I think it is as good as I'm going to get, at least for a long time. Again, I've heard very few that I think were noticeably better-sounding, and then only if you are being "golden ears nit-picky". I'm more likely to be tweaking and upgrading that TT, than pursuing any upgrades, for some time to come.
As back-ups and for playing other carts (Mono, 78s, etc...) I have other tables I like, too, including the ultra-rare Pioneer PL-L1, Pioneer Pl-C590, Sansui SR-929, Thorens TD124 (in need of TLC/restoration), a Lenco 75 (working, but awaiting a plinth upgrade), two Dual 1219s, and some other lesser ones I haven't got rid of yet. I'll probably get a Yamaha PF-800 tomorrow, but more for the cartridge on it than for the TT. There are other TTs I hope to get and try one day, but only just to hear them. I am having fun designing a DIY TT, but I'm in no hurry to finish it; it is just for fun, and I don't expect it to sound better than the GT-2000. No, I think I'm satisfied with that one; the rest is just tweaking it and playing with others for fun.
I'll be upgrading cartridges as time goes by, but I'm not dis-satisfied with what I have, only searching for EVEN BETTER sound. More in the nature of tweaking, since things already sound quite good.
DIGITAL SOURCES:
This is where I am still playing around. I just bought a new external DAC, which so far I like (the Musical Fidelity X-24K), and I have some decent transports, but I'll definitely be ugrading this area.
That said, I'm only trying to bring CD sound back up to where it doesn't disappoint me after listening to my best analog stuff. It's getting close, esp. with the better recordings. I'm satisfied with the analog, and digital at its best sounds good enough to me, too. Just trying to make the lesser digital recordings sound better, which falls more under "tweaking".
I'll be heading towards storing all my CDs on a music server in the next year or two. I think the quality of digital stuff and the price (for terabyte discs, for example) has reached the point where it makes sense to do this seriously, and especially so after I get the CD source/DAC to where I want it, so I have good enough sound to store in the first place. I'll probably add a TOTL squeezebox, as well. [Note: I have iTunes and an iPod, but only for convenience of music on the subway, etc... I definitely don't consider it hi-fi, nor very important to me!] But again, to me this is more like tweaking; it is something for convenience and fun, and it doesn't bother me in the least that I don't have it right now. I'd rather spin vinyl, most of the time!
AMPS:
I do intend to upgrade here, one day, to something more "spectacular" to put between the GT-2000 and the RS-IIs, but again, I'm content "enough" with the sound of the Soundcraftsmen 5002MA, the Adcom 555s, the Sansui BA/CA-2000 set, the Marantz 3650s + 300dcs, the Yamaha M2, several Chinese-made tube amps, and a few others. Again, while I plan to upgrade eventually, it isn't urgent to me, because I am not dis-satisfied with what I hear. I like to compare different amps with different speakers, but feel less need to do that as time passes, and I've tried more combinations.
I haven't even touched on receivers or tape sources, but I have to go to work now, so I'll cut this short (well, shorter...
) . I'd say I'm blessed to have the gear that I do, and I'm satisfied enough that my emphasis these days is more on getting rid of lesser stuff and just tweaking out the best that I already have, than anything else. I'll be shifting towards DIY projects for fun, and putting more emphasis on the software -- the LP collection and putting the CDs on hard disk -- rather than pursuing more hardware.