It's under $500 so not an extreme expense but I argue that it falls under the NNN maintenance purview, responsibility of the tenant.

A bit more expensive and financing may be an issue.  

Generally, hard money is expensive you want to borrow as little as possible and pay it back as soon as possible. 

Not looking to build a huge portfolio or anything, just want a warm place to escape from time to time as well as an eventual retirement location.We are a bit overwhelmed and looking all over the place. 

Question: Since Airbnb pays me directly, does he get to claim my payout as an expense?

For context, my property is in a flood zone so flood and wind insurance are extremely expensive.

Ultimately, it all boils down to you—your experience, your availability, and your ability to handle multiple tenants, units, and issues (trust me, they'll all come knocking).Typically, for beginners, anything beyond a duplex can be overwhelming.

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23DSCR lenders generally let you vest either individually or as an LLC.

You're just feeling overwhelmed and that's normal. 

I currently manage the property so, I know that the operating expenses amount to $67,204 annually.I've done some research and found that the cap rate in our area typically falls between 7-8%.