Overhwhelmed and don't know how to cope

I'm 46, and my boyfriend and I have been together for over six years. He is the most kind, good-hearted, intelligent man -- and he loves me so much, as I do him. We met when he remodeled my house and have been together ever since. As I got into the relationship, I found out that he was somewhat of a hoarder -- seriously, you couldn't walk in his house, it hadn't been cleaned in forever. I have since learned that he saves everything, doesn't pick up after himself and has an entire backyard full of dead cars, scraps of building materials -- you name it -- all stuff that he thinks he'll use one day. Despite the fact that he is a master carpenter, his beautiful 1920s bungalow is falling apart and has never been renovated. I also came to find out that he had never paid income taxes -- having started out in his teens working for cash in the construction trade, he could never get organized enough to pay taxes and once he hadn't paid for a few years, well, then the whole situation was completely overwhelming. He was constantly getting his electricity cut off or his phone cut off or having to drive back from an out of town job to pay his car insurance (he has no credit cards because he can't manage them and gets into debt).

Of course, I didn't see the severity of the problem. I thought love conquers all. I have a well-paying, stable job, my own beautiful house. We bought a vintage travel trailer to renovate, Paul thought it would only take a couple of months. We bought some land together... with the idea that in our partnership I could purchase the property and he could fix it up. Eventually, we'd have some real estate to support us in our retirement years.

He'd been in therapy for 10 years, but still was facing many of the same problems and obstacles. After a couple of years he was diagnosed with ADD. Of course, I'm a take action kind of person, whose work life depends on me being organized and able to approach things logically and step by step. I thought that if he gave me all his money, I could make sure all our bills got paid. We merged our phone accounts, and our auto insurance. I made all the payments on the properties. (He still had his house)

Then, the nature of his job hit home. Construction is a stop, start business. You have a job, then you don't. It takes work to promote yourself and line up work so that you can have a new job when an old one ends. Needless to say, Paul didn't have the skills necessary to maintain steady work.

I won't go into all the details, but we've ended up in a bad place. And I am as culpable as he. Year after year, I've ended up paying his property taxes ($7000/year), back mortgage payments ($2,000/month), etc. -- talk about co-dependent. I'm overfunctioning to his underfunctioning. While still being responsible for my house, and our other properties. Yet none of our long-term projects and dreams have come to fruition. He can't seem to get it together to make progress on any of them. Meanwhile, our vacation home (more of a shack really, we bought a serious fixer-upper) has become a junkyard -- filled with dirty laundry, trash, filthy, and the beautiful view of the high desert is obstructed by piles of odds and ends of building materials. We bought it with the idea that we'd rent it. But after 4 years, the roof still hasn't been replaced (even though it needs to be quite desperately), no renovations have been done. And he still hasn't paid any income taxes. He has no health insurance (but smokes two packs of cigarettes a day). It is as though he lives in an alternative universe where no normal rules apply. And he simply doesn't seem to understand that he can't actually afford his house. I even paid for his therapy with an ADD specialist -- until I couldn't afford it anymore.

He's at a tough point in his life. His building job ended in the middle because the client ran out of money (the bad economy). Then a friend backed out of renting his house after he spent two months working 12/day trying to get it ready for her. Then the new job he had lined up fell through because the woman was worried about the economy. I want to be supportive, but don't know how to do it. I know he feels so much shame that he is in this position. I told him a couple of months ago that I would give him the proceeds of a couple of old cars that we had to sell and then he was on his own with his house. He understood, but I know that he's feeling abandoned a bit.

I'm at the peak of my career, yet broke. I can't afford to travel, I can't even enjoy the beautiful property we bought. My dream of what our life together would be like, a partnership where we each contributed equally in our own way, is dying. I think I am going to have to sell two of our properties.

How do I "re-separate" our finances? How do I say 'Honey, I know that you have no work, but I'm not going to pay for your phone, car insurance"? How do I let him know that he can't ignore the tax situation forever?

How do I get him to remove his stuff from our vacation house, so that I can enjoy it. The reason the place in the desert is so energizing and peaceful for me is that it is a big, empty chaos-free place -- yet now, it's so full of stuff and trash that I break down and sob every time I go there. And how do I negotiate with him to ensure that there aren't constant broken promises (good intentions, the road to hell ...)?

How can I be loving and have boundaries? I want him to look for ways to mitigate the effects of the ADD on both himself and on me (organizing strategies, tools, whatever works). But it doesn't seem like he ever gets there. Just the same behavior, resulting in the same results. And he works so hard, so long, and it seems like he never makes any progress. I know he's exhausted and frustrated too. And, I know that he hates being dependent on me -- and I am pretty sure that I've come to be a crutch.

He's caring, kind, loving, and devoted. I want us to grow old together. I have great compassion for him, but I need help. We have to find a better way to live.