A new tenant might not pay rent, need to be evicted, do damage etc. 2.

We use a spreadsheet to track any deductions for issues caused by tenant damage.

The damage is north of 150k.

We’ve had to replace two window sashes (tenant damage) over several years, and it was so easy to order and replace just by having Lowes order it by the actual number, was only like $125 each time.

I received an insurance payout for a damaged roof on a rental property and the contractor doing the work is offering a discount for cash payment.

I feel like I’m opening the possibility of problems with a stay over, or the place is left with damage and cleanliness problems without recourse.  

And as far as the relationship advise, is that kinda like saying "hey you know your girlfriend kinda looks fat in that dress, you should probably tell her that" or something along those lines? 

It looks like damage to me versus a faulty stove (no damage beyond the glass) and we would not be liable.

IS it worth investing not only 70k, but the brain damage and the time it takes to achieve the desired return.

If it is due to a condition of the property (multiple losses, unrepaired damage, etc.) it will be more difficult to get a regular company to write it.