I used to have CoStar with my previous company, but no longer have access. 

A lot of investors are jumping to secondary lines of insurance coverage and the problem with those is that the companies are based in the Cayman Islands or the Bahamas a lot of the time, and it is suspect that they would actually pay out if the need arose unfortunately.   

In other words, your personal holding company isn't terribly relevant to the discussion.

My managment company has made more than a reasonable amount of attempts to get the HOA to have this repaired. 

Another option would be a co-living arrangement utilizing a company like PadSplit.

They mentioned that the family member began debt consolidation 20 months ago, the way debt consolidation works the company lets it go into collections I am concerned that if the person files for bankruptcy.Even just one of 3 family member file a bankruptcy 7, can they stay 3 to 5 months without paying rent?

My partner and I have a General Construction company (CSL).

Now some food for thought.

My business partner owns a roofing company but has weak credit and more limited cash flow.An LLC is a common choice for partnerships since it protects personal assets and simplifies tax management.

Quote from @Dyllon Gibbs: Hi All,Does anyone have experience with rent guarantee insurance and any specific companies?