I figure I save $5-6k per year with high deductibles and by paying that $5,000 loss out of pocket.

@Michael RossiIf you are doing a no doc, LLC loan you should have no issue with getting a cash out refi.If you are going the conventional way and using your personal credit, if you have less income, a job change or loss could impact getting approved in the future.Overall, I would not consider this to be a major factor in your decision.

So here we are with the Fed continuing to raise rates to destroy "demand" (yes to create job losses) and if they stay the course, we could see rents decrease as fewer people are able to afford the rent, which would increase supply.

My advice is to Not to be in a hurry trying to make up for what you think is loss time.

Loss of Use (for the costs if you have to live elsewhere after a covered loss)4.

A hundred bucks loss is one thing, but you have likely lost 6 figures in cash flow in these 8 years. 

After the last crash, it took ten years just to recover the losses.

can you share the math that indicates that loss?

In addition, if you are not a real estate professional, you might be taking additional losses in your real estate that you can't deduct. 

I think I’m dealing with a management company, is there a chance they would like to off load this property before year end even at a loss to avoid paying taxes and such?