Here’s the situation...I have a friend who was a very hard worker all of his life and has been battling a fairly severe health issue for many years while still working. It finally got to the point to where he had no choice but to leave his job and sign up for SSDI. He was approved without issue due to the legitimacy of his condition. I state this to convey that this isn’t a case of someone milking the system and wanting more. That said, he is now in a position where he can’t physically work but is going stir crazy from having so much time on his hands and is not drawing anywhere near his old salary. I am a buy and hold landlord and from what I have read, he can earn “passive income” but Social Security’s definition of “passive” seems to differ from the IRS’s. I have proposed that if we can figure out how to do this within the rules, we would form a partnership to buy and hold properties. He would handle the lead generation/marketing stuff and some other “back office” stuff and I’d be the “boots on the ground” and mange the properties. He’s a very tech-savvy guy and has excellent sales and people skills. So...I guess what I’m asking is this...is there anyone on this site that is currently on SSDI that is successfully investing (within the rules) that could give us some advice or direction on what steps we need to take to make sure that he is able to remain qualified for Medicare in case his condition worsened.