The quote I got from my primary residence insurance provider is quite high. 

Consider your comfort level with managing several mortgages and the risk of vacancies vs a slower but potentially more rewarding path to ownership.

And *not* junk, they provide you value - a lower rate.Rest assured you'll get an expert on the phone and a great rate(points or not) driven lower with technology from Lower.com. 

So, this leaves a bunch of smaller lesser known insurance providers.

@Calvin HaywardReal estate agents frequently provide closing presents to purchasers and vendors as a signal of gratitude and celebration of a thriving deal.

Get with a good agent who understands short term rentals because the more of these you do then you can scale the insurance under a Business Owner Provider Policy (BOP) and then you don't end up with a dozen individual policies out there for each property that cost you a fortune.

Even if you're not making much profit at the start because you're investing in a better area, it should work out fine.If you're losing $100-200 per month but have a stable job, you should be okay.Most people get rich with real estate through property value appreciation rather than cashflow.If you're comfortable living with roommates, you can purchase a house in a good area you like and rent out spare rooms.

As mentioned above, the University provides a lot of different types of renters like grad students, recent graduates, professors, health professionals and stuff.

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

So, they would refinance your current mortgage and then provide the 95% LTV HELOC.In my situation with the option they gave me it doesn't seem to be far off from my current mortgage, I'm currently with rocket mortgage w/ a 2.8% ARM and to refi with Lower (in order to get access to the HELOC) the new interest rate would be 4.1.