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I can tell you that I've been doing tons of paperwork and applications dealing with things for my mom. A lot of applications ask, "has any property been transferred within the last 2 years". So yes, even if it's sold, there could still be repercussions.
One thing I forgot to mention-if his property is paid off (or close to paid off) he should probably be eligible for a reverse mortgage. You might want to check into that. His property could actually provide an income for him.
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