The sooner you start these conversations, the better prepared you'll be when the right deal comes along.Local professionals can also be an invaluable resource.

On June 7th, we sent an itemized list of deductions via text; he responded on June 8th, disagreeing and threatening legal action.

If, however, there are any gaps at all in any of the above items, even a gap so small a mouse can squeeze through, that tenant will exploit it and your life just became a 7th Level of Dante's Inferno.....:)

Here's a https://www.irs.gov/businesses/cost-segregation-audit-technique-guide-chapter-4-principal-elements-of-a-quality-cost-segregation-study-and-report to the IRS website noting specific items that are included in the cost segregation study report. hmm, that website is a 404 error.  

If a storm happens immediately after you replace the roof, the actual cash value is the same as replacement cost, so you've lost nothing.The only thing you would have to worry about are items you did not intend to repair

This will give you one critical piece of information, that it may take X days to get an offer and sell, and the second item will give you what your competition is right now.

Also, how old are your capex items? 

Often times they come back with a list of repairs that they would like to see to protect the home or mitigate liability. 90% of the time those items were on our list to fix anyway, and sometimes we even haven't done before we get the letter from the insurance company.

But I just want to start the conversation so we can negotiate the terms so it's beneficial for both parties.

I have had many conversations with her friends about the differences in our markets and  have recognized for a while now that there may be some mutually beneficial opportunities to work with Canadian investor specifically.