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A couple of things come to mind: he needs to be reassured you will handle this for him, Not to worry. I would let him be in on it by giving weekly or bi monthly updates and getting his blessing to proceed.
If possible save 2 or 3 very special things from his Grandparents. If this is not the case, order a trash bin from waste management and start tossing. You may find something of at least sentimental value and of value to your family such as photos, antique guns, etc. ( My Mother had shoes in original boxes from the 30s. I figured what she had not used in 60 years she was not going to miss, especially since she had dementia and couldn't see from macular degeneration. But you never know.)
You need to gauge his awareness of the house situation by asking test questions. Pick something he may have always been interested in-- like sports, investments, cars, whatever-- and ask him a pertinent question. If he seems overwhelmed, confused, or over it, that would seem a sign you could move forward.
All the best to you:) xo
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