Curious living situations

One of the criteria that you can specify for online dating is the person's living situation. It's not something that comes to my mind immediately. But then, there is that whole stereotype around mama's boys. The implosion of the dot-com era also changed conventional assumptions about kids living on their own after graduating from college. So the question today is - should a guy's living status matter? What does that imply about him?

I mention this because Is is dating a guy, HardHat, who lives with his sister and her husband (there might also be kids). They have been dating for around three months. She's told me bits and pieces about him. He generally sounds like a decent man - tall, handsome, beard (which he temporarily shaved off because she hinted she wanted to feel his bare face), attentive. Initially, her biggest dislikes had to do with his car and living situation.

If I remember correctly, HardHat is a project engineer. Because he manages construction teams, he drives a pick-up truck. She told me that his reason for choosing a pick-up was to match his workmen. It makes sense that he would want to build respect and a sense of equality with his workmen. Driving up in, say, an Audi or Honda Civic would not make a favorable impression. Because Is grew up in the South, she has negative stereotypes about people who drive pick-ups. She's embarrassed to be seen in HardHat's car. A couple times, she has asked him to drop her off across the street so that she would not been seen emerging from a truck by co-workers. Several of us have tried to explain that the image of a pick-up owner in California is different. In Southern California, many guys think they're cool and convenient for surfboards. She knows it's a very superficial thing, but it bothers her.

The greater sore point is his choice of living situation. Is would like to see him be more independent. (She may also be factoring in the knowledge that HardHat is a native of the area. Besides never living beyond a 20-mile radius of his birthplace, HardHat's never really traveled outside of California except for a few business trips. It's the idea that he's not very worldly.) She doesn't understand why a man in his 30s would choose to live with family (versus alone or with roommates) when there's no obvious need (and I can't remember what reason he provided to her).

In her most recent e-mail to me:
"... long story short, they got kicked out of their house b/c the owner wanted to sell the house and instead of moving out on his own, he signed a lease to another house with his sister and family. can't date someone who lives with this sister/family. i said if things progress further b/w us, he needs to change that arrangement in 6 months. otherwise, things won't work."

I haven't talked to her yet for more details. I can understand why it seems odd. I certainly would question why a 30+-year-old man lives with his parents in a non-temporary situation (think KT).

- Is there a family need such as a disabled child?
- Are they an unusually close knit family?
- Does the family have financial reasons?

This is a topic she'll need to tread carefully about. I don't think she should or could force this issue. He will need to decide this for himself. I'm not sure what I would do in her shoes.