I doubt that he's ever thought about it all that much, since he doesn't seem all that bothered by it. I don't think anyone else has ever thought of this as a problem. He has ex-girlfriends, but we've never really discussed if they ever thought this was an issue or not, and if they didn't, then I wouldn't be surprised if he's just accepted this as a part of who he is. Which is fine, I've done so myself with a lot of my issues (which does unfortunately mean that they're harder to unpack now that I want to, but that's neither here nor there), so I can understand why he's done so if that's the case. But that would also mean that he's never thought of this as a problem that requires a therapist. But I don't know, we've never talked about it in much depth before, so maybe I shouldn't speculate so much.
Yeah, I agree that we need to sort things out both together and individually if this is going to work. I'm honestly just concerned that he'd think that I'm trying to change him into what I "really" want if I start poking at too many things at once, or that I'm suddenly heaping criticism on him out of nowhere, so I realize that I'll have to take baby steps and be very clear that I'm taking care of my own baggage at the same time so he won't take it the wrong way. But I do feel that there's a lot of stuff we need to unpack before us living together would work.
He's two years younger than me, has a job and while he doesn't live on his own yet, he handles so much of his own household chores that he might as well have been living alone. He did mention going to a therapist for a brief time, a long time ago, so he's not completely opposed to therapists in general. Just as a point of reference, I've lived together with people and on my own since I was a teenager, I'm a full-time student juggling a couple of side jobs (which barely cover my rent, but eh) and I've handled most of my economy for years now (my parents help out with some things, like paying for my insurance).