I have literally heard wealthy people complain at length about the difficulty of finding a reliable gardening service for their mansion. Should I listen to their concerns without judging? Or is it reasonable to dismiss their misery? (This is a rhetorical question.)
1. The implied belief that there is a cosmic measuring stick for how good someone has it, but, more importantly, that this measuring stick matters. The judging accomplishes nothing, other than to let the person judging feel internally superior for a moment. The more relevant issue is letting that judgement cloud any rational decisions you need to make later with respect to the people you're judging.
2. If you're making policy decisions, then this cosmic measuring stick of suffering would matter (like taxing gardening services, I guess?), but are you making policy decisions?
3. Do you need something from them, and does that inform how you'll behave towards them regardless of what you actually think of them? Startup founders who didn't come from rich backgrounds experience this all the time around VC's. But it's not really possible to keep the functional motivation and the desire to fit in entirely separate.
4. Are they just complaining because shared lightweight misery makes for fun socialization? People who aren't rich do that too. The content may just be a function of their environment.