Sennheiser HD650 / HD6xx ?

That sounds like a job for the Meze 99 Classics, Your first description in title fits it like a glove.

Costs about 300 bucks. There's also options for balanced and unbalanced upgrade cables from Meze, going from 100-250 bucks.

I own these myself, always an easy listen!

I think the ZMF Atticus may fit your criteria, especially the exaggerated mid bass.

sennheiser HD599

Koss

I guess, it won't hurt to try a chi-fi IEM. My daily driver rn are KZ ESX. Dirt-cheap, non-fatiguing, a bit bassy around 200 - 300 Hz and down. Pretty decent overall.

to mwe the lcd-2 sounded way better than the X bass wise. im using an ifi gryphon with just xbass (no xspace) and the switch on bass and presence which was lovely. the only ting ive found i prefer is some of the higher end meze isodynamics

> I can’t play my speakers past 11pm (for reasons I won’t go into)

gave me a good chuckle

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650/6XX sounds like the recc. Maybe not nearly as much mid bass as something like a Meze; but it will completely thrash and destroy it in all other metrics. The 99 Classics are absolute trash.