The main "goal" of house hacking is subsidizing or completely eliminating your housing expense through renting out other portions of your home. 

Super high interest but if you're only talking 30 days or less, shouldn't be too expensive. 

HI Hernan,You can always start off by house hacking meaning you live in one UNIT or ROOM and renting out the other vacant units/rooms to offset your monthly mortgage payment.There are several ways to run and make sure you are maximizing your rental income while keeping your living expense as low as possible.

Not to mention the emotional toll it takes on a property owner and the aftermath of finally getting your property back then perform expensive repairs.

Sounds like you're smarter than the average bear, err, arbitrager. :)

Actually a bigger problem for me is that my average nightly rate is showing at $620, which is my highest daily rate.  

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.

As we get to retirement I expect our expenses to reduce for example today we have a home mortgage in retirement I would expect to pay that off. 

Right now we just have a separate personal account that houses our rental income and expenses.

To add to what Bill Gulley posted, up to 40% of tenant's income may go toward housing expense / rent, but that means that you only can get rent above HUD's FMR of like 10% of the tenant's income.