There could also be hidden costs, additional liens, or property issues reducing auction value.

So with all that, I'm thinking to open booking now for next summer with a 7 day minimum, see how it books out, and by late winter/spring I can reduce it to a 3 day min to fill any remaining weekends, and then work on filling mid-week vacancies as summer approaches.We were leaning towards Fri-Fri, but Michael I like your suggestion about the Mon-Mon option, which could be nice because renters would have the weekend to travel and then begin their stay on a Monday, then they would end their stay on an upnote with a long weekend...But with either Fri-Fri or Mon-Mon renters would probably need to take 6 days off work...Sunday-Sunday might actually be better because renters would only need 5 days off.  

Perhaps not the best example, but  what you are doing is no different than a medical patient who walks into 6 doctors offices with a broken finger asking to be treated with radiation.

He talks about how you can purchase a rental property, manage it as a short term rental during the year you acquire it, do a cost segregation study, use those "losses" to significantly reduce your taxable income that year, and then turn the property into a long term rental in the following year. 

The actuaries realize they have too many policies in one area and the insurance companies want to reduce risk and spread risk. 

By living in one unit and renting out the others, you reduce your living expenses and generate income.

Increasing your down payment can indeed make the asset cash flow positive, even if it reduces your cash-on-cash returns.

It’s just 7 miles from the beach, 2 miles from a large new hospital and medical campus, and within 2 miles of the county government offices.

If you ever found your self in trouble you sell a property and reduce your debt load and obligations. 

I should look at house hacking as a way to reduce my living expensesAll of that makes sense to me but in my personal situation, I live with my parents for free.