What would make a nice man from a normal, uncomplicated, middle class family choose to keep getting involved with women with so much baggage?

It’s because women without children (or baggage as you call it) would prefer to start a relationship with a man who also doesn’t have children. Whether they want children in the future or not. It works both ways.

Maybe it makes him feel superior, maybe he thinks he can "save them". Only he can answer that question.

Sometimes though, the more stable your own background the least likely you are to understand the harm an unstable one will be. A lot of men are inherently selfish, sadly, and don't look at things through their kids eyes (or more of them would be paying maintenance, for starters).

I think you need to drop the whole thing about his first wife having "done well for herself" - he picked her because he could impress her. It was HIS choice as much as hers.

I have a brother like this but it’s just accidental really. First wife cheated on him and they split with one child. Not his fault. Then, as he was older, many available partners have children and as he co parents, he found they understood his situation more and it avoided women without children who might resent a step child.

He had a very conventional upbringing but circumstances led him down a different route. But not a worse route, just a different one. I think we all need to understand that there are many ways of living and no one has the monopoly on ‘right’.

Maybe he does, but it's not always easy. Over a particular (not certain!) age most people have kids. A lot of people are already married. Add to the fact just meeting/chatting up someone now seems more unusual than dating apps, and it's hard, because not many good people who want a family won't have already settled by that age, which means most will have what you call "baggage".

I’m simply trying to understand why someone with a stable upbringing would repeatedly enter into such chaos.

Are you sure there's not something up with the rest of you, as opposed to your brother?

People are different. Most families have at least one 'black sheep', but most don't care about it beyond saying 'oh that's Uncle Terry's latest partner, who knows how long she'll last'.

You seem curiously put out by this, as if it's a personal reflection on your family. I'm beginning to feel a little sorry for your DBro. Can't have been easy to be the loopy, 'unstable' one growing up in a family of paragons. Whereas the reality is that lots of people are a bit doolally and they're happier if surrounded by others who are also a bit doolally.

he has a Saviour complex?

Sounds like me but the reverse
am well educated, great well payed job, decent well brought up children, middle class background

I choose absolute lunatics, bedecked in red flag banners

I am too embarrassed to go in to the details

done the Freedom Program etc, still did it again

im now staying well away from any men to try and break the habit of a lifetime

You seem very set on his upbringing somehow dictating how you think he should date. My upbringing trained me to leave school early, marry a local tradesman young and be a SAHM to a large family. Instead I got four degrees, married someone similar aged 39 and had one child by choice.

my question is why he has chosen to create this for himself when it’s not how he was brought up, there was no need!

First thing that comes to my mind... he's 'different' from the rest of you in some way (ADHD, BPD, something else or maybe just his personality) and his upbringing didn't meet his particular needs though it may have worked fine for the rest of you. Some ducklings just don't walk in a line.

Let him get on with it. It’s his life NOT yours. He’s already divorced with a child, he will inevitably meet someone of the same status.
Mind your own business and get on with your own life!

Maybe the thought of being in a relationship with the someone who has the same mindset as his family is horrifyingly boring to him?

He is choosing women he thinks he can "save" possibly. Women marry up and men marry down, generally. A lot of that is because men want someone they can feel superior to, so as his life gets increasingly complicated with exes and step kids, perhaps he wants someone with worse so he can feel less messed up?

I think it’s just a case of you overstating how desirable your brother is and how “wholesome” he is.

firstly, is he even attractive to the women you perceive to be worthy for him? Because you then go on to lay out a pattern of “unworthy” women being with him, maybe that’s what he attracts?

secondly, maybe instead of women seeing him
as a meal ticket, he just likes the power / control? Many men feel more comfortable in a traditional gender role relationship and feel threatened dating an ambitious woman / higher earner etc. He might like them being dependent on him

and finally it could just come down to sex? If ultimately they’re both attracted to each other and are meeting each others needs, he might not care about a woman having kids already.

Only to people with narrow minds and low self esteem though

Agree. The DB probably feels suffocated.

I'm a working class woman with one dc. Is this how people see women like me?

I think i have a bit to offer, great chat, love of food and travel, love of learning, can pick out the perfect gif - what a lovely reminder that to some, youll always be seen as beneath them 😬🤷‍♀️

He has trouble sustaining long term relationships and so attracts women who also have trouble sustaining long term relationships? Otherwise, they'd all (your brother and the women involved) be looking for partners with different qualities altogether.

That's my take on it anyway. If your brother isn't what you would consider 'nice', 'normal', 'stable' and 'baggage free', he isn't going to attract women who are these things either.

Sounds like your db has his own baggage too.. doesn’t sound like the catch of catches to me.

What is the actual “baggage” and “chaos” that you’re referring to? It sounds like you mean the mere existence of the children and perhaps shared care?

Who exactly are you expecting him to date? You don’t say how old he is but at a certain point he’s unlikely to meet women who don’t already have kids.