It seems to me that he knows that the relationship looks creepy, and he is making an effort to not actually be a creep.
With the age gap and the income gap, he knows that he will be accused of taking advantage of her relative youth and relative poverty. So he wants to make sure that whatever happens, happens by mutual consent. (Not as romantic as sweeping her off her feet and ripping off her bodice, but then, bodice-ripping can have legal repercussions if it turns out that she wasn’t in the mood.)
It looks to me as if neither one of them is completely certain of what they really want. Which does not improve the odds, but does not necessarily doom them.
I once worked with a woman in a similar circumstance. He was substantially older, much wealthier, and when she needed a place, he humbly gave her a spot in his home. It was all platonic, though he was pretty clearly interested.
I admit I was suspect, all along. I could see what he was hoping for, housekeeping together, sharing moments, intimacy increasing and soon, he’s where he wanted to be all along. It was so overt it was a little creepy to me. When they shifted to dating/living together at rocket speed, I thought he was a pretty smooth player.
They are happily married, with kids and a house, for over 20 yrs, to this day.
There are all kinds of ways for relationships to begin, so I don’t think it’s right to judge, based solely on that.
Having said that, I would answer, "Yes, obviously money matters - especially to you! That’s why you’re compelled to keep asking about it, it seems to me.