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He keeps the spaces he doesn’t use fairly clean... BUT, boats, cars, trucks, food (COSTCO)... He lives alone. If he can’t FIND something he HAS, he just buys another... How do I approach this issue when he “Feels” the items are “worth” something even if he doesn’t use them or they go BAD, (food)...

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Ah, I feel for you.

My mother is also a little hoarder, but luckily(?) she can no longer drive, so she is hampered a little by not being able to leave the house alone, to shop. She 'online orders' crap from every catalog that comes. She gets 4-5 packages per week. Her little apartment is stuffed to the gills and she has a basement full of more stuff, which she only let me put in bins, to store, when my one and only attempt to "organize" her went south.

My advice? Don't do a thing. Just like any other mental disorder, unless the person WANTS to change, they won't.

To a true hoarder--a can of soup has the same "emotional value" as a Ming Vase. They can't differentiate between what is "nice and needful" and what is, well, "crap".

You can ASK him if he wants help sorting, and of he does, good for you. I would not hold my breath. All you can do is make sure he has a safe exit from his home. And that heaters and such are not blocked. Just basic safety.

BTW, Mother owns over 100 shite blouses/shirts. She is basically housebound now. Still buying more.

Mother has some dementia, but this hoarding is as old as I am. Her home of 5,000 sf was emptied over the course of 3 years and she has effectively hoarded herself in her 800 sf apartment, over the years.

What's "claustrophobic" to you or I, is "hugging" to a hoarder. We've cleaned and cleaned and she just blows up at us. Not worth it.
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Mthr was a hoarder. She was greatly motivated when I set firm boundaries. I think she was going to "show me" when she hired someone to shovel out 3 rooms ( the furniture was simply tossed onto another layer of furniture upstairs and completely shut off access to that floor). The man who did it said the rooms were up to and over the top of the door frames with just a hole to crawl through. 

8 years later when were rescued her the level was about 4-5' from the floor, in the low spots. She had the worst hoard our hoard cleanup specialist had seen, even though some was cleared 8 years previous.

Hoarding is very much like an addiction and the person is not likely to change even after hitting rock bottom. Wait for a crisis. There is a Children of Hoarders site you might visit.
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My Dad is a hoarder too, poor Mum putting up with it for years. He can't do anything now but he still won't get rid of all the wood stored in their hall for DIY jobs he'll never complete. Boxes of tools, shirts, shoes, expired medication, papers, books you name it he keeps it. 5 unusable vaccum cleaners. Dining table covered in "stuff" can't see any wood. Kept all his bank statements/payslips since year dot! The house will be a nightmare to sort through eventually. I feel for you !
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I believe a lot of people don't understand the difference between hoarders and junk collectors. Hoarders have emotional attachments to stuff and would not sell that pristine Apple I for a billion $! A junk collector will sell things for a reasonable, un-ego filled price. Compare the stars of Hoarders vs the guys who star & sell in  Pickers.
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One of my brothers is a hoarder, has been for years, certainly no dementia at work. It’s one of the strangest psychological phenomenons I’ve witnessed. He actually mourns anything that is thrown away, even when it’s worthless. And our family has certainly learned there is nothing we can do to change the behavior. Make sure he’s safe, but otherwise leave it alone, it’s not fixable
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My Dad is a hoarder too. It got worse after his mother died and he had acreage to store stuff. I have to use clear garbage bags and he has to see everything that goes into them. If I can find a 'safety' reason to toss something, he is more likely to let me toss it. The shredded curtains at the French doors were a tripping hazard, so I could toss them.

I estimate there is 3-4 dump trucks worth of junk to get rid of on the property.

I admit that I have hoarding tendencies, but I do not have the emotional attachment to stuff. I have a fellow helping me clear out stuff and it is great to see my home looking like a home again. Regular garbage and recycling is not a problem, it is the stuff that has to go to a special location for disposal. I used to have an agency that would pick up stuff for the thrift shop, but they did not show up three times in a row, then blamed me for not leaving the items for pick up. Yeah right, I am not supporting that charity again.

I have an arrangement with the fellow who is helping me. If there is something he can sell that I do not need, he is welcome to sell it and keep the cash. If I planned to have a garage sale to make some money off the things, it will wind up in the garage for a few more years. Out the door is better for me.
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If you watch the shows (and I've watched a bunch of them over the years), it seems like most hoarders start hoarding after a loss - like a parent or a child dies or they lose a beloved job. And it's one of the hardest mental disorders to treat. People are very resistant to change. It also seems to run in families, but it would be hard to determine whether it's learned behavior or a genetic predisposition.
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HEY!!!!! I'm a hoarder and I don't have dementia. ;)

There's hoarding and then there's hoarding though. I've noticed it's quite common for the elderly to hoard paper. There's paper squirreled away everywhere. If he's holding on to a used napkin that he got a restaurant 10 years ago that's one thing. If he's holding on to a pristine Apple I computer, that's investing.

I often buy something I know I already have. Why? Because it would take me longer to find the one I already have then it would be to buy another one.
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Have you ever watched any of the shows about interventions with hoarders? It's actually a mental health issue and not readily cured. It seems to be challenging for the hoarder, even when they are highly motivated. Like, they have to clean and get rid of stuff or the city will condemn their house and they'll be out on the street. But, even under those conditions, the hoarder remains steadfast.

In light of this, I'd consult with a professional about it. That way you can get some guidance and tips. Honestly, I'm not sure that I would be up for it. It's a huge deal to get a hoarder to change. I might try to make sure things remain safe and contend with the bulk of the problem, when the hoarder is no longer able to maintain the household.
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A few years ago I picked up a workbook-type "Helping the Hoarder in Your Life" or similar title book at the library out of curiosity. It was sadly eye-opening. The author, who was either a social worker or psychologist, basically recommended a strategy of harm reduction, managing, minimizing, as hoarders lack basic insight into their problem and can't really be helped, unfortunately. It was not a hopeful, uplifting read.
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