Worth it IMHO.I agree with @John Underwood that it shouldn't make too much of a difference.You can always charge the guests less and then expense the difference.

Your letter is different if you are targeting long-time absentee owners or homeowners.

They are two very different strategies. 

Angie,The best way to start is to buy a primary so you can take advantage of the lower down payment.

The qualification for "hard money" and a loan for a primary residence (meaning where you actually live) are very different.

I am in the process of moving to FL where I have 2 short term rentals. both with mortgages on and the new Primary will also have a mortgage.

I asked that I wanted to turn my primary into an investment property and make the next home our primary over the next year while renting out the rooms then leaving for another house again at the end of the year.

Are there any other "untapped" Ski Resort Towns that can provide Value as well as Cash Flow, with Cash Flow being the Primary Goal?

We are running numbers on two different deals right now in Carbondale.

As I am in California seeking property in Pittsburgh with over 90 different neighborhoods, its very hard to tell which are the safer ones, but area vibes helps alot.