Legal Question in Real Estate Law in Illinois

Can't say for sure - insufficient information. If there is an HOA with townhome declaration you may be simply townhomes with separate insurance rights/obligations meaning this would go through your own insurance, or a 'condo townhome' with an association responsible for roof issues as a common element where the association's insurance would be involved as to the roof and damages caused by the roof, and YOUR insurance MAY be involved as to the interior. If there is an HOA, either way, you should be in touch with them and your own insurance agent. If the HOA is responsible for roof integrity, then this could be an emergency situation they could get some immediate protection for to prevent further damage. If the HOA is NOT responsible for roof issues, you may have to initiate this yourselves. You sound like you may need an attorney to review the community documentation to clarify your rights AND obligations. Also, you may have some difficulties if this condition is the result of deterioration or neglect as (a) it has been allowed to fester for some time and (b) most insurance only covers "events" like if a tree fell and punctured the roof or there was a fire that caused the hole -- not just because things age and/or have deferred maintenance.