E and O will almost always settle. and for the agent its usually a 5k deductible at least when I had it for my company that's the way it went.. and then it goes away.  

I would check what your deductible is and ask them if your rates will go up if you submit a claim....?

If our kids go with us and we drive to LA on a Sunday, all of our direct car related expenses are tax deductible even though the kids are in the car including 1/2 of the meals for my wife and I.  

There is a fairly new 20% pass through deduction you may qualify for that could help you, but not everyone qualifies.

Increase deductibles: Raising your deductible can result in lower premiums, but make sure you're comfortable with the potential out-of-pocket expenses in the event of a claim.4.

But, what about all the deductions like depreciation borrowers say? 

I thought it would be better to throw a new post here about the rent deduction question.

Similar green energy investments could be considered if you can make the numbers work (credits on some types of low income housing can be north of 50%).Depending on how long these properties have been held, they could consider implementing cost segregation studies via a change in accounting method to accelerate some depreciation.The operating proceeds could be re-deployed into new properties where cost segregation is an option to accelerate depreciation to offset proceeds.If the properties are low basis and we are not maximizing the 199A deduction, maybe considering an S-Corp structure for management to be able to participate in retirement plans and also generate wages to use as a 199A base. 

I have brokers in various states where vacation homes run into deductible issues, HOA reserve issues, litigation, just to name a few examples.

Short term rentals might offer different deductions compared to long term rentals.Risk Tolerance: Assess your risk tolerance.