OP some of your descriptions of your DH had me genuinely wondering if you had hooked up with my ex especially the stonewalling (refusing to discuss problems) and the availability to others at our expense.
Likewise I had considered him laidback during our initial time together whereas now I realise he was so out of touch with his needs that he'd go along with whatever anyone asked of him. Which was a lot. In fact, I used to feel very irritated on his behalf by what others asked of him. For example, he'd spend a weekend wallpapering a colleague's living room simply because they'd asked. Or pick them up from the airport, stuff like that. Stuff that everyone has to deal with - including us. But time and again I'd be left with the kids while he did chores for others, people who never helped us out, not that we'd ever have requested airport lifts or free handyman services.
And I, like you, am an organised, tick-box sort of person. No wait, I was a control freak. I really was. So yes, we drove each other crazy.
We tried counselling, lots of it, but our relationship continued to deteriorate.
I felt that he didn't engage, that he attended and said what the counsellor wanted to hear, but reverted the moment we left her office.
As I tried to improve myself by being less controlling and more assertive, he stepped up the stonewalling to the point where I wasn't allowed to open any sort of discussion at all and we were essentially living a false life.
He moved from passive aggressive to aggressive, culminating in awful, drunken rampages and I asked him to leave.
In hindsight I can see how we were both screwed up and created a whole new screw up in getting together. When I shook the foundations by trying to grow, it all came unstuck.
So I'm guessing that if you both want to save this relationship, you both need to do the work. Hard when one person is a stonewaller.
Looking back I think we should have separated much sooner. Because once the standards of behaviour slip, the rot seeps in and it becomes increasingly difficult to salvage the relationship.
All the best OP. You can't make someone change but you can be clear about your expectations and standards.
I would be leaving his family stuff to him, not reminding him or in any other way playing into that crap.