The end of nagging - but what comes next?

How do you stop nagging - or reminding? 

I don't feel like it's my job to help him remember to do things. Yet there are things that he's taken on that he won't let me help with. Those things sometimes have a time-sensitive component to them, so if they are not done in the time that they need to be done, there are consequences. 

For example. A year ago (YES an entire year), we started looking to buy a house. It's a year later, and our broker has to keep asking him for the same documents because by the time my DH gets them to him they are already expired (bank statements). I asked about this yet again this week and he assured me it would be done - has it been done? No. If you added up all the times I've asked him to finish this process it would probably number in the thousands. Something that would take one afternoon AT BEST has taken him an entire year. I told him this last time I would not ask him about it again because I was frankly tired of it. And I can't take it over because he would be super offended!

Another example. Ten years ago he told me that our storage of garbage (yes, literally garbage - stuff that's broken that he's been meaning to fix for two decades, including baby toys for our almost 21 year old - would be cleaned out. Ten years later, now we have two storages full of garbage. If I ask him about these things, he flips  out. I can't even talk to him about it. So I just keep paying for it. 

One more example (I have lots more, but....). He has no insurance as I am self-employed and can't get him on my insurance, as he has diabetes and high blood pressure. He refuses to look for insurance. When I asked him about it today he acted like I had grealy offended him by daring to ask him about something that could greatly impact our family's financial situation. If he gets sick - which is a very real possibility as he takes terrible care of himself - I will be paying for it out of pocket. He's been sued twice by doctor's offices for not paying; he doesn't show the bills to me OR he tells me that they are taken care of, which they are not. 

I don't want to nag. I don't want to be negative. And I can't just let him face the consequences of his decision (as Melissa's book likes to point out) because it's not him that will be suffering the consequences. He does not care or just ignores it. I guess the only solution here is just to pretend everything is okay? I'm so tired of wanting to rely on him and it's just not happening. I guess maybe that's where the nagging really originates.....I want so badly to have someone to rely on.

Bottom line: how do you handle NOT nagging.