I find the iPad a bit bulky to be considered portable anyway, but my commutes are done standing in someone's armpit and then changing to another train and standing with someone in my armpit.
If you want a desktop system and you are bound and determined to use an amp/DAC, there are myriad choices. The HP1-P1 I've not used, but I assume it's pretty much the same as the Cypher Labs Solo outboard DAC. To be honest, the iPad by itself has a decent sound, one that is competent and in some cases, better than some amps out there.
You'll have to go somewhat high up the ladder (quality, not necessarily price) to better it. For hard to drive earphones, a simple iBasso T3D would drive better than the iPad will naked, but will have a bit more background noise. A cheap Line Out Cable and a cheap, but good amp will do the trick for about 150$, or thereabouts. You can go all the way up, and do a HP-P1 or CLAS and amp of your choice, too, and only probably enjoy the thing more, but be tied to a desk or bedside.
big big big.
EDIT: As for outboard DAC's, you can use almost anything that has battery power. I've used dozens of DACs with the iPad, some as cheap as 150$, some as expensive as 1500$. As long as the mains or battery is powering the DAC, no problem. The latest I've used and really really like is the ~300-400$
GoVibe VestAmp+.