@William Coet, as Jackson noted, there are too many variables to even begin.Two things to remember, any tax losses you utilize to offset incomes, will reduce basis making bigger tax bill in sale year.  

A decent down payment and good exit strategy will reduce my risk. 6.

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. 

Creative FinancingFinancing can be a challenge in tough economies, but several creative strategies can make deals work: Seller Financing: Negotiate with the seller to finance part or all of the deal, reducing the need for traditional loans.

I am curious how many people reached out to a local flipper and said "hey can i shadow you and check in on projects for you doing drive-bys and inspections or make calls to coordinate subcontractors".. 

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

Welcome out of the shadows!

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.