So, this is where I come for advice, eh?  Let's give it a shot.

Home Setup: Sony Vaio Laptio --> HRT MSII --> Schiit Asgard 1 --> DT880 (250)

Work Setup: Desktop --> Audinst HUD-mx1 --> DT1350

Vinyl: Pro-Ject Debut Carbon (Ortofon 2M Red) --> Pro-Ject Phono Box USB V --> Onkyo Receiver --> Pioneer SP-BS22-LR

My past headphones were Grado SR80i and SRH 940s.  I liked them both, but eventually found them to be too thin-sounding.  I know a lot of people feel that the 880s are a bit dry and analytical, but they sounded extremely musical to my ears after my time with the other two headphones.  After listening to the 1350s, I now know why people have the impression of the 880s that they do.  While I may prefer the 1350s warmer sound (in comparison to the 880s), I'll still keep going back to the 880s due to the open-design and bigger soundstage that it brings. 

I honestly have no idea what to upgrade next.  All I know is that I have the "itch". 

I've toyed with the idea of the HE-500s, but that's a BIG expenditure for me and I don't know that I have the equipment to drive them properly anyway.  I've thought of upgrading my amp (Lyr, maybe?) with the possible idea of getting the 500s down the road.  The Bifrost has also been on my wishlist for ages.

I'm pretty content with my work setup.

As for vinyl, there are a couple of cheap turntable upgrades that have been on my wishlist for a while, so that's tempting as well.  Namely the Speed Box S and Acryl-it Platter.

So, help me out people...take my wallet and spend my money!

 

Asgard can drive the HE500 no problem. I think that's your best path.

Although the turntable upgrades are a good idea if you can only pick one.

Here's a doozy, pirates. I am looking for the best easily available master of "A Night at the Opera" in either DSD or redbook format (disc or download is fine). I have the DVD-A but no way to play it at my desk with my main rig.

EDIT: Nevermind, Burns beat me to it.

I have the 2011 remasters done by Bob Ludwig (from the original tapes) -- and they are good. I'd bet the Hoffman ones are good as well. Probably can't go wrong with either of them.

I've heard a lot of people say that the Asgard would get plenty of volume out of them, but wouldn't show their true potential by a long shot.  If I got the HE-500s, I would probably look into something like an Emotiva speaker amp eventually.  Or possibly the Lyr.  But, I'd be stuck with the Asgard for a while at least since it would take plenty of time to gather more funds.

I'm not really feeling let down by any of my setups.  This is nothing more than the curiosity of what else is out there.

Is the Bifrost something that wouldn't make a huge difference due to the rest of my setup?  I've always felt the allure of having a nice Schiit stack to look at.  Plus, I'd like to get away from USB-powered gear like my MSII.

Still, when it comes down to pure sound improvement, it seems like the headphones will have the biggest impact right now.

Always upgrade the headphone first. The HE-500 is very good, but if you favor the open sound of the 880 you might consider saving up for the Sennheiser HD800.