Also contact your insurer and see if they offer a STR policy.

Not to mention if there is a premises liability claim amongst many other incidents that could arise at your property, the plaintiffs attorney will file their claim regardless of who the true owner is because it’s the insurance money they are chasing. 

With proper property management, it's not an issue being out of state.You can work with a turnkey company or directly with builders that offer the same services for your first property.

For me to offer more advice I would need to know more about you before I start prescribing.

Another reason could be to lower insurance costs as you will be covering less.

I offered one tenant $50 for the truth, and he told me that the options were to pay $900 per month with a check or $600 per month in cash.

Therefore, even if an applicant acknowledges her credit history and offers a larger deposit, landlords must adhere to the legal limits set by the state.

I have a particular interest in islands, as my long-term goal is to captain a catamaran and offer tours for snorkeling, sunset cruises, etc.I'm interested in places that offer great ROI without being overly expensive.

They would do insurance. 

We don’t require but advise tenants to carry renters insurance which they usually don’t carry.