I prefer the 800 to the 800s as I like a bright top end. I’m still dithering about paying that much money even for second hand. The 800 range, for me, is the most comfortable headphones I’ve ever tried.
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I had the original HD-800 for a while and enjoyed them alot! I have been through most of Sennheisers serious hifi headphone range between HD-598 and HD-700 previously but they all failed to impress me. (Just not my kind of sound) Then i found an opportunity to try out the much adorned HD-800 and i really liked them. I liked them so much that decided to take one step further to the HD-800S which are a little bit more “meaty”. I do prefer them, but to be honest, the original sounds just as good and have perhaps even a slightly bigger sound stage.
The HD-800S also works beautifully with the Hugo TT.
And you may very well be correct, the TT2 has got more muscles to drive difficult headphones! 
For sub 400, I would normally pick up something from Drop (formerly MassDrop). But, you are in the UK and the prices are not good.
I am a big fan of the HD-650, but those cans are a little finicky with respect to the amp and source (they can sound veiled). Instead, let me recommend the newer Sennheiser HD-660S. I have 7 different sets of 'phones and the 660S isn’t my best pair, but for my collection, they are the best all-arounder.
Headphones are a VERY personal thing - lots of subjectivity involved. It does help to audition, but in my experience, you need to live with a set of headphones for a couple of weeks to really decide if they are for you. As they say in Head-FI: “Welcome to Head-Fi. Sorry about your wallet.” You’ve been warned.
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if you are ever in London there is a headphone boutique shop, an outshoot from Spiritland the HiFi cafe, where you can try on a lot of hi-end cans to see if you could live with them
The website is being updated when i looked today but
https://spiritland.com/location/spiritland-mayfair-headphone-bar/
an overview
Just registered my intrest thaks
I am in London nearer to Christmas so may pop in.
Where are you normally Paul, if you don’t mind saying?
I live in Manchester, I’m visiting London to watch a show. Will be staying in the city centre somewhere.
Not advertising ourselves at Grahams, but we’ve got a few different headphones for demonstration here. The Hugo TT 2 is always plugged into our Roon Nucleus+!
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I do really like the look of the HD800S but fear they wont get the use they deserve. Looks nice, is that a seating area in the background?
HD800 has been my main headphone for the last 6 years , retirement pressy from wife to keep me quiet
They are simply stunning on the right material but are rather unforgiving on sub standard source material.
I use an Audio lab M DAC as headphone amp streamed via RpI and Digione
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I’ve used LOADS of headphones, and currently use a TT2.
I currently own Senny HD800’s, Beyer T1.2, DT1990’s and DT1770’s.
BY FAR the most versatile, and consistently pleasing sound comes from the DT1990’s. They’re great with all genres, and are also within your budget.
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Think you may of hit the nail on the head 
I’d really try the bayerdynamics beforehand they clamped on my head far too hard to be comfortable.
Ged, Give the Ether2 a whirl. Very light, and excellent sound.
Other than being 4x my price limit it looks great 
$500 doesn’t get as much as it used to. Massdrop has had some good options in the less than $1k offerings. In a couple of days, they’ll have the Senn 6xx Sony Wireless combo for $400.
I’m not the OP I was just expressing my lust for hd800s. My trusty second hand 650’s will do me for the foreseeable future.
I have HD800 and HD800s. Great cans.
Cheers mate, rub it in lmao.