So this is not what I do, take with a grain of salt… but if I had your use case, I’d probably get a FiiO M11 plus, and be able to be mobile. It’s a Roon Ready endpoint, and you can get up & go to the fridge with it.
If I was going for a more dedicated rig, I’d do separates, because upgrades happen. Pi + your DAC, then get a Schiit or Topping separate when the time is right.
I started with the most basic Schiit Stack on my desk (Magni + Modi). Now, upgrading one piece at a time, I have:
Pi → Schiit Gungnir → Schiit Folkvangr → Sennheiser HD800
→ Creek 5350SE → Harbeth P3esr xd
Now the “B” speaker taps of the Creek also feed a pair of HiFiMan he6se (v1s) which are a crazy load (need a lot of current, hence the speaker taps).
I couldn’t make either of these phones (which I love very much) work without real amplification. The Folkvangr is also bananas - in a very different way.
So my advice is either - get an all-in-one that optimizes for something simple and get the advantages (like a DAP) or get separates and allow yourself to go down that path. Don’t get stuck in the middle. My 2 cents.
(Oh and the Schiit Modi + Mani from eBay is a remarkable value, really truly suggest it as a gateway drug)