The longer they limp along, the more the condition worsens, tenants stop paying rent - it turns into a downward spiral. 

Anyway, back to the original topic.....This current economy and the worsening economy that is arriving, does not mean anything to veteran investors.

@Grant Lovelady- thanks -  yes you are  right - terms on rental property loans are  high ( especailly the loan fees  being charged )  - things  worsen  for " cash out refinance " loans  ...most HELOC lenders  arent  interested in providing HELOCS  on rental  homes  ....if you  are talking about  getting a heloc on your primary - this is indeed  likely the  best  path to get   some capital ( rates for a OO heloc  should be in the 8.25% -10% range  with  very low fees 

The risk would be the loan would be a loss if rates remained the same or worsened in 12-18months.. to me this seems low risk. 

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.

Without talking to one, you'll always be in the dark and could worsen the situation by taking a wrong step. 

Statutorily raising the cost of labor above what the free market will bear will likely worsen unemployment, drive business toward automation and robots, and worsen the lack of opportunity of many of the unskilled and lower classes.  

So far, I'm doing the latter although I do let them know, if things worsen, they may have to seek legal advice. 

Your question is perceptive for what many investors in 2020 face, as being invested in the stock market, while facing the fact that in 2020 the U.S. is in Recession, with this Recession is likely to worsen in 2021, which at some point, will cause a correction in stock prices.

But all tenants were and are long term renters.With one, the neighborhood changed (worsened) and he no longer wanted to rent there.One lost her job and ended up having to downsize.One was dis-satisfied with the pest control I provided (I really did try to work with her on it but spraying every single month was simply not an option.)