Did it twice more once for breakeven and once for a loss, not to mention my time.  

NY times did an expose on insurance company losses that should make you worry. https://www.nytimes.com/interactive/2024/05/13/climate/home-...

This is somewhat hard to follow but I think what you're saying is that your business partner filed a personal articles insurance claim and they ran a loss history report on your partner when applying for insurance on this duplex?

Can I see a list of loss runs for the past 5 years?

Yes, you lose the value add upswing, but you also reduce potential money loss and time loss.

To me, the best thing you can do is find a buyer who is willing to buy them from you via a quit claim deed (even if it's at a loss) so that you can start over.

But also working with them if there is a job loss or a roommate moves out.

Two are being forced to sell at a loss this month.

Sometimes before even asking a specific question, they will start rambling a rehearsed excuse story on their credit, previous landlord troubles, job losses, etc.

Our revenues have not dropped due to weather, but if we did get hit hard by a hurricane it could, rather would cause losses in rental revenue.