"When I asked him about where he'd live when he's retired and not working to pay his rent he said he'd always planned on living with someone so the cost of living would be halved. He's assured me that he wants nothing from me and would pay half of everything and he's not concerned with getting married or not, he said it would be up to me to do whatever made me happy."
Always planned on living with someone. Anyone, really. Well, not quite anyone - anyone who can provide that place to live. But yeah, anyone. You'll do. You can be the adult and I'll be the manchild/exotic and expensive pet.
That's quite the admission! 'Nah, I'm not looking after myself, I'm going to leave that to somebody else.' It's very optimistic of him. What if someone/anyone didn't materialise in time? Or not at all? What would his Plan B have been?
"I'm very conflicted because his personality traits and qualities he has are wonderful, he's not materialistic or shallow etc but I feel scared and insecure about his lack of a later life plan and lack of financial security."
Well I'm sure he's very charming in the current situation of interviewing for a Sugar Mummy, but do you think the mask might slip a bit once his feet were under the table? I do. And actually - he is shallow. And as for not being materialistic - he certainly expects someone other than himself to supply the material goods of living, so yes, he's materialistic too. He might not be bothered about owning the materials, but I do believe he will be quite insistent that he have access to and the use of someone/anyone's material goods.
So to answer your question - it does not matter that he's broke. It matters that he expects this to be remedied by someone/anyone else.