Need to build a headphone system

Greetings, and welcome to the headphone community. I dove into head-fi in 2015 when I moved to Japan. I too, have listened to many headphones on the market.

The previous two suggestions, the Woo WA5 with Sennhieser HD800S is a very good suggestion along with RAAL SR1B. I have listened to both many times. Both come from two opposite sides of the spectrum to reach what you are looking for. I would definitely do your research and listen to the RAAL system prior to purchasing. This is not a HP you buy unseen. As far as the HD800, yes I truly believe paired with Woo products decreases the brightness and provides a very good listening experience. Personally, I would not purchase the HD800S unless you pair it with a warm sounding tube headphone amp like the Woo. I believe both HPs will work fine with hearing aids specially the RAAL since you can adjust the wings.  

Now, let me throw in a 3rd suggestions, which will provide you yet another polar spectrum close to your price range. A electrostat system consisting with the Blue Hawaii SE (BHSE) and electrostat HP of choice. I am currently a proud owner of the BHSE with the Audeze CRBN. This system will run you 10K, but you can shop for a HP within your price range such as the Stax 007 Mk2. Now, electrostat system naturally is notorious for being analytical specially pairing with Stax, hence why I own the Audeze CRBN. Although, with the BHSE you can swap out tubes as needed to reach your desired listening pleasure.

https://www.headamp.com/products/blue-hawaii-se

The HeadAmp website will provide you info on the HD800S, RAAL and the BHSE with electrostat HPs. Not sure you location of residence, but I would recommend visiting https://thesourceav.com/ in Torrance CA. This is one of the few places where you can listen to all three suggested systems. Spent many hours in that place.

Good luck, and again welcome to head-fi.

P.S. If you ever come to the decision to purchase the BHSE/CRBN combo, speak to me and I may cut loose my personal system for your price.

Thank you all!  This is is all really helpful.  I'm in New York.  Does anyone have experience with Audio46?  Although I expect there will be lots of home trials, a good store would be helpful.  (And FWIW if I find what I want in a store, I'll buy it in a store - it's hard enough being in business without being a showroom for the internet.)  I am partial to tubes, so I'll be checking out Woo and the VM-1A for sure.  This is going to be fun! 

The best place for RAAL info is head-fi.com, where Danny and Alex the 2 principles of RAAL-Requiste help out.

Raal Ribbon Headphones - SRH1A | Headphone Reviews and Discussion - Head-Fi.org

RAAL-requisite CA-1a Circum-Aural Ribbon Headphone is here! @HeadAmp | Headphone Reviews and Discussion - Head-Fi.org

I’ve been to Audio46.  It’s pretty small — not surprising being in NYC — but they have good stuff and the people are nice and accommodating if you wanna listen to stuff.  And their prices are competitive if u wanna buy.  Great HeadFi resource to have and you should definitely go.  Just make sure they have something you’d like to listen to available to demo if there’s something specific you’re looking for.  Of course street parking is a challenge so be prepared to pay for garage parking.  

I visited JS Audio in Bethesda, MD and they had a RAAL system. I live in the Washington DC area. I have not explored elsewhere. To bad you did not go to CanJam NY couple months back.

After my posting last night, I believe the RAAL system may be what you are looking for. It’s basically putting 2 ribbon monitors on your head. Coming from a 2 channel environment its an easy transition. Keep us posted.