Its caused him to go in to extreme debt and he just needs to get this handled. 

$400,000 seems extremely high for a rental property.

So make sure your uses of the refinance money conform to business  purposew if you want to write off the interest.This method is commonly used in a 1031 consolidation exchange. 

Settling is common and you often don't do anything with older properties unless the foundation walls are coming in. 

This is very common so don't feel discouraged by maybe having to do some "inner work" or whatever you want to call it.Hope this helps!

Not only will you learn different neighborhoods, how to manage people, and costs of construction, but they can get paid extremely well if you get good and know how to work with the City.

Quote from @Bryant Brislin: Land in the path of development that may seem a little far out, but your gut/intution and common sense from an urban planning perspective tells you that some day, whether it's in 10 years, 20 years, etc it will be a great long-term position for your family to have and hopefully sell at a signifcant multiple return compared to what you've paid for it.

From purely a lending perspective, the projections from AirDNA and Rabbu are the only commonly accepted sources for underwriting a short term rental purchase or refinance DSCR loan.

I have to think a ski town is all about STR  not the opposite They currently have about 100K in the bank that was to be used for a common space amenity, but I suppose could be used for enforcement legally. 

In some cases, if the ARV is outlandish or the change in value is rapid and extreme (ex: purchasing for $100k last month, appraising for $500k thirty days later), it may need to be supported by a CDA or evidence of repairs/upgrades.