Kyle there are a ton of options here that you can compare.

Free option available too.    

This might give a one-time (non-scalable) boost to cash flow, offer multiple value-add options, and allow the house-hacker peace of mind, via the assumed mortgage, in long-term breakeven or positive cash flow in the event that the value-add plans end up not being executed, and/or the person has to move out, and rent by the room or STR become unavailable for some reason at a future date.

We also had the option of another type of policy that was even less expensive that would have required us to spend at least 1 night in the house and rent it at least 30 nights each year.

With your income and the option to use an FHA loan, buying a home could be a smart move, especially if you plan to rent it out later.

Having only the guarantor screened and closing in an LLC are options. 

In this case S8 is probably not a good option.If you are convinced you can find a great family that will take care of your property, then either option is fine for you. 

Health insurance payments, Health savings account lots of options. 

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One of those options is to let the tenant know you won't renew their lease, then offer them the opportunity to leave early if they find another rental.