Also, what's covered by this insurance.

Based on what other places are rented for in this area, the rental income will likely cover more than half of our estimated monthly fee (mortgage, property taxes, etc.)I'm wondering if anyone who owns a property in this area has dabbled in AirBnB and what their experience has been like?

I can team up with couple of agents but  Roofstock or HomeUnion are working probably hundreds of agents therefore would cover more markets.

Often times the rent will cover or exceed your mortgage costs.

He is looking to move in with his SigO but is concerned his rent wont cover mortgage/expenses.

The difference being that the buyer's policy does not cover total replacement if the house burns down and it essentially just covers your investment in the house. 

If a claim were to happen while the property is vacant and being renovated/repaired, the insurance company would not cover it if it's insured on a landlord policy.You need to purchase a vacant property policy. 

For success, any expenses that will be covered out of your pocket, must be re-couped from the tenant's rent over the year. 

Personally, I find spending $300 on some decent landscaping in the front of the house, and taking some good pictures do more for finding tenant than lowering prices. if you're willing to lower rent by $50, then why not just spend the $300 on prettying up the place and get the depreciation that equates to the lowered rent. ($50 x 6 months = $300)just my $.02 

It is a great example, but if you cover your costs, you are killing it, taking home extra cash would be a windfall.