In the professional audio world, which I am more familiar with, we face the same kind of issues. Once upon a time there would be separate devices in a recording or mixing studio, such as :
1. Microphone Preamps
2. Line level Mixers
And the end result would then feed into
3. Analog to Digital Converters.
4. With the end result recorded on a computer
5. Played back via a Digital Analog Converter @ line level.
6. Which feeds either speakers, a mixer or directly and indirectly into a headphone amp --> into headphones.
So this was the "separates" model, different devices, and you could mix and match from different models of gear and manufacturer. Or upgrade a single component in the signal chain.
Then things changed, and we now have these ALL in ONE devices aka audio interfaces, which never existed before, which are all singing, all dancing, and integrate all of the items mentioned above. The down side is, many of these are built to a cost, with compromises. Good in some aspects and average in other aspects. For example many "professional" and "prosumer" audio interfaces have headphone outputs with impedance above 20 ohms, which I consider not suitable for most IEM's and probably not suitable for any OE Headphone below 150 Ohm input impedance. My solution for this has been to not bother trying to get an Audio Interface that is good for everything, which would cost a lot of money, but to purchase a very headphone amp, which can be relatively inexpensive, in today's market, and pair this with inexpensive audio interfaces that excel at everything else except the inclusion of a low output impedance headphone amp.
I think of the current trend where many DAC devices are similar, integrating headphone amps, but these also have compromises, typically not being able to drive easily the most demanding headphones. My thoughts have been - think of any headphone amp on many of these integrated DAC's as a bonus item, their main feature is the DAC function. And rather than trying to get a DAC with headphone output that will satisfy ALL headphone purposes, consider purchasing a dedicated headphone amp, if you ever think you'll need to drive any headphones with lots of voltage/current/watts. Furthermore with these ALL in ONEs, whenever better digital converters are available, these are introduced in newer models, so you have to junk the entire device, and buy a new one, when the only benefit of the more recent model, is the DAC and/or ADC
Almost any decent DAC with a headphone amp will drive most IEMS and OE Headphones adequately, and therefore one does not have to spend too much on such a DAC/Headphone amp combo. Then have a dedicated headphone amp, for any exceptional scenarios like headphones which need lots of oomph to drive them, which most people will not need.
It's a similar story for anyone with an electrostatic headphone. The headphone amp in any DAC, becomes redundant, cos you need a dedicated headphone amp for your super demanding/special electrostatic headphone.
So for the vast majority of IEMs and OE headphones, any decent DAC with a headphone amp will do. Demanding dynamic or planar magnetic OE headphones, will need a beefier dedicated headphone amp, and electrostatic headphones will also need their own separate amp.
If budget permits, only reason to have a combo DAC/Headphone amp is convenience, otherwise - just buy separates - a DAC and a Headphone amp. In my estimation, the incremental cost, compared to a combined DAC/Headphone amp is in the region of $30 to $100, and the dedicated headphone amp is likely to have much more oomph than anything in a combo device. The separates will most likely address lots of scenarios such as balance and unbalanced inputs to the headphone amp, as well as balanced and unbalanced outputs from the headphone amp, will more flexibility to pair this headphone amp to any DAC.
I can't see how much more headphone amps will improve, so the headphone amp will retain its value, and if one so chooses, one can upgrade just the DAC device in the chain. This I think is really the better solution. Separates. Providing lots of flexibility, to upgrade or change only a part of the chain.