Basic questions for newbie

I mainly stream Qobuz into pi2aes/Roon to a Schitt Dac/vtl integrated amp. But I listen late at night after wife has gone to bed, keeps her awake. Vtl has a headphone out but is about 10’ from where I sit (Long cable, heavy?). 

I have no experience in headphones. What are options I should pay attention to? Do I just plug headphone in amp? Or run from my surface or iPhone ?  Or ???
I also use Qobuz and run the Apple Camera Adapter from my iPhone or iPad into an Audioquest Dragonfly Red portable amp/DAC into a pair of HifiMan HE400S ‘phones and works really well at home or on the go.  Just one option if you’d rather not run a long cable. 
If you like the sound out of the VTL then buying a longer cable seems like a no-brainer?  Most good cables are really lightweight.  You will never get better sound wirelessly.
Thx. Ok so if a longer cable isn’t too big a pain, then now what about headphones? I have no clue about them...
What speakers do you have?  What aspects of sound reproduction are most important to you?  This can help narrow down what type of headphone might work best.