For electronic music, nothing touches my Sony MDR CD950 > Fiio E7 (high gain, eq either 1 or 2) > Crystal Piccolino IC > Source, absolute punchy and tight bass and fast sounding for a half vintage too. For the same genre if I wanted a bit of air and comfort and tad bit of speed for faster electronic music my Sr-Lambda Pro's > SR7 adapter > either my modded VK2100 or my modded Meixing Mini EL84 tube amp does a great job while having similar sounding qualities to the Sony. Both these combo's best my HD800, LCD2 rev.1, FA-011, HD600, MDR CD850/3000 in regards to this genre.
For classical/jazz, my HD800's Anaxilus felt modded (following Tyll's recommended thickness) > 4-pin XLR Balanced Crystal Piccolino cable > Beta 22 (2 channel passive ground WIP mod to 3 channel active ground and new enclosure) > Ross Martin DAC > optical out > Creative X-Fi Fatality Pro in my desktop/Audio Request Nitro Pro music server. I tend to swap between my Lambda's and my HD800's when it comes to certain classical waltz.
For all the other genres with vocal's, LCD2 rev.1 internally Crystal Piccolino'd > 4-pin XLR Balanced Crystal Piccolino cable > Little Dot MK VI+ (various tube rolling) > Balanced to my Ross Martin DAC > optical out > Creative X-Fi Fatality Pro in my desktop/Audio Request Nitro Pro music server (Honestly I hate swapping out cables every now and then depending on my mood of what I want to listen to).
For Metal/Rap/All rounder genre's, HD600's/FA-011's/FA-003w > Few balanced and single ended pure silver and Canare cable's > modded Chazz II/Bottlehead Crack(in transit)/Darkvoice 336 SE (various tube rolling) > few sources as mentioned above.
Portable 'end-game' is none existent for me atm, but I'm quite satisfied with my ES5/IE8/IE7 > GSP Voyager > Rockboxed 60GB Gigabeat
I'm deciding now whether I need another DAC for one of the above listening 'stations' as I have two digital out sources my desktop and my Audio Request music server.
As for can/amp, upgrades I don't think I will for the time being or many many years to come, I will be curious as to what new and future headphone's will sound like such as the LCD4's, HD900/1000 (or the new Sennheiser electrostat coming out) etc. Might end up getting a Dana Zeux or WA22 if I move back to my HP rig's after I find my end-game speaker setup.