It costs them nothing to fix it and you have a year warranty so you’re not getting a mechanical discount. 

That is after all expenses: Vacancy, repairs, Management, evictions, Lawyers, Accountants, the list goes on and on.

So, this is putting him in the position to have to look at the possibility of doing a 1031 exchange on the 2.5 - 3.0 million that would otherwise be taxed at capital gain rates (he wants to avoid paying Uncle Sam at all costs).

I am only asking her to move out for 6 nights but what she is demanding will cost me ~2/3 of the rent.

My property manager provided a quote for repairs.

Since we own the property, the only costs (hopefully) will be in converting the whole attic into a studio.

It costs more, but installs fast and is typically better quality.

Inventory should be higher near you with rising insurance costs and that could mean decent deals, but don't jump too quickly.

If you remove this covered peril, you're removing wind damage coverage to the entire building, and not just the roof.Your assessment of the deductible seems accurate, but I can't speak for the replacement cost of a new roof. 

This can cost you 10's or 100's of thousands in property value/sale price.