Need new headphone setup.

How much portability do you want?  Your iPad is already a streamer, so I would just buy a dongle DAC, like the Dragonfly Cobalt.  If you buy a streamer, DAC and amp for headphones, you're likely limiting your listening to one location and eating up a chunk of your budget (since you're essentially building a second mini-system).

I have several headphones and DAC/amp combos and, frankly, my cheapest, Dragonfly Black and Grado SR80s, sounds pretty damn good.  The Black, the new SR80x and a USB/Lightning adapter would run you a bit under $300.   A Cobalt and Grado 325x would run around $650.  Lots of headphone choices out there - but keep the source simple.

Thank you very much for your suggestions.

‘Sounds good to me.

Holmz,

What do you mean by “using the IEM without a pad?’

I have a good headphone amp in my DAC/preamp, but for portable use I highly recommend my alternate setup, which I run from my phone or laptop. It sounds excellent.

A good set of budget reference phones like my Sennheiser 600 or 650 (Massdrop, now called Drop, does runs of these at a great price). $330 on Amazon Amazon / 650

and...

Audioquest Dragonfly Cobalt DAC/amp

review

Building a HeadFi system is like building a mini “big rig” so the same principles apply.  That said, what sound characteristics are most important to you?  This will help narrow down your choices for headphones, then you can go from there.  But, to answer your question — yes, you can build a surprisingly good headphone setup for $1000 or even less, and I think you’ll be surprised how good it sounds assuming you take the time/effort to choose the right gear.  If you share more about what sound characteristics you’re looking for you’ll get some good recommendations here.  FWIW.