Thanks for the welcome everyone!

@ db Cooper - As far as headphone stuff goes, I've been lucky enough to get a pretty wide exposure to gear from living in Chicago (large metro area, a good number of large and small meets). I've personally owned lots of Sennheiser phones (HD580, 600, 650, 800, HD25-II, Amperior, Momentum), some HiFiMan planars (HE-400, 400S, 500, and 560), a couple Oppo headphones (PM-1 & PM-3), modded t50rp mods (LFF's Paradox, Slants, Enigmas), a few Beyerdynamic phones (DT-1350, DT-250 250 ohm, DT-880) and piles and piles of assorted mid-fi odds and ends (V-Moda stuff, Koss Portapros/KSC-75s, Sony MDR series phones, random bluetooth headphones, etc. etc.). I haven't owned any Grados (too bright for me) or E-stats (because $).
Amp and DAC wise, I've heard and owned a crap ton of different setups. Stuff thats stood out to me and I've thought really sounds great: I really like vintage Marantz & Pioneer Receivers (with speaker taps & an HE-6). Other favorite chains I've liked have been a Schiit Yggdrasil > Ragnarok > Audio Zenith PMx2, a Questyle CAS192D > DNA Stratus > stock HD800, & a vintage Parasound (HD1600) > Bryston BHA-1 > Audeze LCD-3.
My own setup right now is a modded Sennheiser HD650, sourced by a Schiit Gungnir (Multibit) with a few amping options to switch between depending on the mood (Schiit Valhalla 2 & Mjolnir, and a Bottlehead Crack + Speedball). I also have a Oppo PM-3 for on the go. No world beaters, just a setup with good value for the money spent.
I'm trying to stick to digital audio for now, but I'd *love* to move into speakers and power amps when the budget allows it. I figure this community will be a good place to ask for advice once I start making that move.