A mix.
On one hand, he had more privilege (whether through lineage, hard as it was to reaffirm it, or individual work, or opportunities opening up) than the Warden. He's never wanted by the law in Act 1 (lets forget Mage class for a sec), he is wealthy in Act 2, and he's the city elite (and Free Marches nobility) in Act 3.
But on the other...weighted hard... he suffers a lot. A lot. The Warden may have been set for death and facing the dread of a Darkspawn invasion, which is definitely dire, but I feel that at least they could have comparatively more happiness in the meantime. Hawke? He steps up, then gets bashed down, then steps up again, then gets bashed down.
However, we have to keep in mind that DA2 is set over the course of several years. Frankly, for many people, several years contain at least some hardships.
-Pre-prologue Lothering is nice, outside of losing his father, but is then attacked and Hawke and his family must flee. Loses sibling and endures a cramped boat ride to a place he's never been to. Waits for weeks(?) then has to work a year just to properly live in the city.
-But then after that, the dire situation is over. Anything he does after that is to fund the expedition to get out of Lowtown, or sidequesty optional parts of his life.
-Act 1, possibly loses sibling (or at least separates from them), but gains riches and elevates family to Hightown. For years, things seem rather comfortable, as Kirkwall can go.
-But then after that, Hawke's mother is killed, leaving him mostly with his several friends he made way back. The Qunari invasion of the city occurs and his home is ravaged but he saves it when almost all seems lost.
-Act 3, Hawke is at the near top of the city and has near top authority and respect of it. He may or may not have an idea of an intact family at this point (depending on sibling outcomes and maybe DLC). He at least forms a makeshift family with his friends, or at least a sort of company.
-With the Kirkwall Rebellion, betrayal of a friend, and evaporation of the class placement he had built up over several years, Hawke's life is clearly nearly shattered. Some things can change the context of this, like certain romances, his set personality (diplomatic, sarcastic, aggressive), who he picked, but he's still pushed down again by the world, as if it never wants him to be truly happy.
-In Inquisition, as far as an adventuring loner (more or less) goes, he's doing 'okay', but with a heavy chip on his shoulder due to past events and the blood magic (first for survival, then for power), and templar corruption (first institutionally, then red lyrium) involvement in it.
Hawke has much of him that feels like 'self-made man'. He could have lost or given up at any point, but he doesn't, and that does bring a period of months to years of relative peace and even prosperity.
IMO Hawke is not necessarily done though.
1)If left in the Fade, there's leading lines that may indicate, in terms of storytelling, that some form of him is not finished. Falling into the abyss in order to learn how to fly, yadda yadda. In my craziest speculation, it involves a spirit form of him returning and being all cool and new and able to transform into a dragon
. Won't be a human Hawke but a spirit demogod one will do!
2)If left on Thedas, he clearly gets involved in some matters in Weisshaupt. With how the DAI and its DLC and epilogues timelines work out, we could very well see him again there in a DA4 or DA5. Not necessarily core to the events there, but optionally involved.
3)If left on Thedas, he apparently, no matter what, rejoins Varric at Kirkwall, finish rebuilding it (I suppose with Aveline, and with or without Sebastian's help, etc) and Hawke may return as nobility of what may be a more secure and healthy setup for the city - ideally, a shining capital instead of a decaying port. He may rejoin with his love there and we can so far headcanon him actually having a happy life (with or without one his siblings, and without his parents) with some of his friends and his love interest.
*Used male Hawke for my case, for convenience.
In summary, yes, I think Hawke had it really hard. But I also don't think that any version of Hawke would want us pitying him, but instead helping him to make our own lives and the world of Thedas better than before. Its his will that has helped disaster happen, sure, but seemingly also great positive potential - again, for his life, for the lives of others, and the world of Thedas. The world is unkind to him, but Hawke doesn't give a f**k, he'll forge his own way (at least as far as he sees things). He happens to at least have the 'privilege' to have the strength and opportunity to do so. An example is his own family line. There's wealth and nobility and respect for the Hawkes, sure, but Hawke still had to do the personal work to establish it again as relevant in Kirkwall. He's a goddamn conservative hero *wipes tear*.
