I'm sure budget would be a barrier to do a STR or MTR but if you had a good market for it, it could be a great way to recoup some of the loss.

I will follow that up with , only get it if you are looking to get into sales and help others, if you are just getting it to buy and sell your own properties, it is likely that a full time agent, with extreme market knowledge would be worth their weight in gold. 

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. 

It's easy to find buyers, not easy to find deals - so a good wholesaler is worth their weight, set yourself up for success by communicating your serious intent. 

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