what is your primary concern? Is it that since he's not 'financially minded' you don't share values, or is it that you're worried that's part of a bigger picture of him being dependent on those around him and unwilling to learn to pull his share of the effort? The fact that you mention him not challenging you intellectually makes me suspect it's the latter. In lots of circumstances it's easy for one person in a relationship to bear the brunt of earning and financial planning -- as long as the other partner contributes in other areas. I might be reading too much into this, but it sounds like you're worried that he doesn't, and doesn't intend to since he's comfortable that way.
I think that these things need to be looked at holistically, and there's no way to judge whether someone is prepared to pull their own weight in a relationship from a post on the internet -- but I really think that living with his parents at 37 is a bad sign. Does he contribute financially and housework/maintenance-wise to the running of the household? And I don't mean in a teenagers-do-their-chores way, but in an equal way that respects the fact there are multiple adults responsible for the household. Some people 'live with' their parents because it's the best choice for everyone involved and they can still develop as people -- however, others do so because they enjoy the luxury of being taken care of, feel no need to pay it back, and are fearful of being adults. After a year, you probably know which one you've got.
I apologise for the long personal story ahead and I HOPE that I haven't projected and it's actually a bit relevant:
I started dating a 26-year-old living-with-parents who had a full-time job but no savings and a fair chunk of credit card debt, when I was 19. I really, naively, tried to be non-judgmental, and believe him when he said he was paying off debt and 'saving for a house', and agreed that it made financial sense for him to live with his parents until I graduated. I ignored the warning signs that he didn't do chores, bought a lot of stupid stuff, didn't respect the sacrifices his parents made for him.
I broke up with him when I was 23 and he was 30 because I had graduated, gotten a job, and saved up plenty to get started, and at that point I found out he had been making minimum payments on his cc debt the whole time. Also, that he didn't want to lower his quality of life at all to be independent of his parents, and that actually, he was quite comfortable being there -- not that he would say that.
We've been broken up 3 years. I'm engaged to a guy who moved 3500 miles to be with me, because he actually wanted to be with me, not just to find a girlfriend who would meet him in his comfort zone and stay there indefinitely. My ex is 33 and living with his parents. He has another (also significantly younger) girlfriend. He's 'saving for a house', but last I heard he wanted to joint-buy a piece of land with his parents so they could build houses next door to each other.
You can only change someone so much, and so fast. If it's just finances he has a mental block with, you can come to the agreement that YOU handle those, and probably be pretty happy. But if it's a symptom of a wider problem of being happy for you (and maybe his parents?) to deal with everything, I think you should be scared.
Also, this maybe isn't true for everyone -- but I think most people want to respect their spouse on an intellectual level, at least most of the time. I'd be concerned that the way you feel about that would exacerbate any resentment you feel about 'looking after' him.