Hi Tim,I am a realtor in the Cleveland market and anytime one of my listings doesn't sell I recommend a $5,000 price reduction every 2 weeks until the property sells.In your case, you might want to reduce it a little bit more because you want to sell before winter. 

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.  

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

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. 

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

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

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.

By accelerating your depreciation schedules, you reduce your taxable income which in turn increases your operating cash flow.