Hi and thank you for your questions. Please permit me to assist you with your concerns.
As I see three separate questions, I will respond to them separately to ensure that I do not miss anything.
The first issue is the fact he hasn't paid you and the HOA sides that this is his issue. Here, if nothing is happening and your insurance is not pursuing you would need to take him to small claims court. This is always your right, and since you suffered injury, you can pursue him personally (even if this is an 'accident', he is still liable for damages that were caused to your unit). Suing him is ultimately your own responsibility, not the HOA, so if they are refusing to get involved you have your own recourse.
The second issue is his dubious position with the HOA. As far as paying his dues that is up to the HOA. I agree that he probably should be paying, but if the HOA treats him as a 'salaried' or rather a service for service agent, it is permitted. But they then have to list him as such. I would suspect that this is permitted unless your HOA bylaws bar this practice, but you could attempt to stop it by recalling current Board members and voting in members who are not going to act in this manner.
Third, the IRS issue a bit different. If this is a 'like for like' transfer, and he is not actually receiving a benefit, there is no 1099 obligation. He is not receiving fees, he is simply not paying anything. Now, you can still report this to the IRS and claim that this is a fraud issue and have them investigate, but this is not a proverbial slam dunk.
Please let me know if I can clarify anything else. Please be aware that I am logging off to spend time with my family for the holiday dinner, but I will return later tonight. Should you have questions I will address them then, but there may be a delay with my response. Otherwise kindly do not forget to positively rate if satisfied with my information. Thank you!