NOTE: No offence meant to anyone; if I've overlooked a point that might cause offence I apologise in advance; these are just some thoughts I had after reading the thread and this week's comics so far, so take with a pinch of salt please.
To be honest, if Winslow- basically Hannelore's 'pet' for his existence in the comic so far- is somehow obligated to make the world a better place just because of the fairly limited 'privilege' he's had, surely Hannelore, who doesn't really do anything but work through her own neuroses and issues by working at a coffee shop, should be held accountable for her own good fortune to a much greater extent? I mean, she's got access to untold funds, and by all means I understand her personal issues are crippling and unquestionably warrant working on however she needs to do so, but surely ALONGSIDE that she could, I don't know, fund something that benefits something, or someone? AIs? Winslow probably hasn't had anything in the way of material benefit from Hannelore's family wealth since, frankly, as a pseudo-iPod he didn't NEED anything except a charging point (of course, unfettered, guaranteed access to said charging point is something less fortunate AIs couldn't rely upon, but May and Momo both have this).
Really, to me, Winslow never really had that much tangible privilege anyway (in general terms- notwithstanding the parallels people are drawing with, for example, Claire's situation, which I can basically apprehend but cannot presume to comment upon, as it's not something regarding which I'm sufficiently knowledgeable)- being a sounding board for the, suffice it to say, intense Hannelore, even if that was the 'contract' (I think these are the terms people use here for the relationship between human and AI) he accepted, can't have been a walk in the park; I recall at least one occasion on which he was panicked on her behalf. Yes, he has a roof over his head- so does May, so does Momo (see the aforementioned charging point mention above also). He doesn't have to work to live there- but existed (until literally a few strips back) as basically an iPod with no autonomy (at least, little that he could physically exercise) and, frankly, little attention paid to him and certainly bordering on no respect given; at least Momo had the eel thing and electric shock system to engender said respect when overlooked, and May, despite her rickety chassis, has the strong personality needed to carry her through pretty much all difficulties she encounters (although it doesn't always turn out in her favour). I can understand arguments that May's always kind of a jerk, and that she might feel sore about Winslow just waltzing in and saying 'look at me!'; no-one likes so see someone's good fortune thrust under their nose when they themselves are having a hard time, but she could have given him the benefit of the doubt based on what he's usually like (although as someone commented, is there any proof they've even interacted before, aside from the fact that Winslow addresses her familiarly?)- to be honest I'm more surprised by Momo, the one we might have considered a friend to Winslow (granted, the point someone made about her having outgrown him is a very good one; nonetheless she's supposed to be well-socialised and might have made more of an effort, or at least been able to understand his pleasure); given she has a social protocol database, surely she could have thought of something further- even if non-committal- to say to him? 'I'm glad for you; I hope you enjoy getting used to it!' or SOMETHING. It seemed more like she didn't want to bother, so didn't. Even if she said something like 'we can talk about it later/ tomorrow/ whatever' it might have seemed less... cold? Can a robot be cold? Either that or she automatically jumped to 'wow, what a jerk, coming in here and bragging about getting a fancy chassis for free', which... doesn't seem like something that would happen in reality? Surely for one to jump immediately to that kind of consideration evinces a want of good-fellowship, at the very least, and a strong tendency towards being curmudgeonly at worst, neither of which characteristic particularly seems to fit Momo- unless, as someone mentioned, this is all heading towards 'check your privilege' territory, in which case it makes sense. N.B. if it IS heading to 'check your privilege' territory, that's fine, I merely seek to imply that, with that end-goal in mind, certain factors make more sense than they otherwise might.