Typically turnkey operators are not in C/D areas so price to rent ratio is not working in your favor. 

As an investor looking to purchase an STR in a ski town, I’m not sure I’d feel that confident in a court deciding in my favor, personally.

Even though it's tough, you'll get stronger and smarter than those sitting on the beach waiting for the tides to turn in their favor.

The problem is these bigger markets are almost impossible to cash flow and to make them cash flow; I would need to have very favorable seller financing terms or a lot more money.

This could give me an option as a house flip if the numbers don't work out in my favor for positive cash flow.Target Returns:Given the higher risk, what cash-on-cash return or annualized return should I be aiming for?

one thing is your lending your money way under what private money should charge. unless your just doing your friends a favor..

That creates a really nice price / rent ratio which is favorable for investors looking for cash flow.

Society and demographics favor smaller units since marriage and child bearing are being delayed.  

I agree that the algorithms favor most favorable nation pricing.  

If cash flow improves, it might make sense to hold onto the property while expanding your portfolio with new acquisitions.Reinvestment OptionsIf you sell or pull equity, focus on markets and property types that align with your cash flow goals:Out-of-State Markets: Research markets with strong rental demand, favorable landlord laws, and higher cash-on-cash returns.