Current financing available, construction costs and how to reduce them, appraisal trends, best practices when building on investment properties, rental values, design trends, how to minimize the construction time, ideal target markets, which city's DOB's are helpful and which aren't, preferred vendors, etc.

If you can't Airbnb it, I would suggest offering them a reduced rate to be able to keep their stuff there for the summer.

If it were me, and I could get some significant cash out or reduced rate, I would do it now.

Bernie Sanders wants a 25% “house flipping” tax levied against investors who sell a property at a profit within five years of purchase.He also wants a 2 percent “empty homes tax” on the property value of vacant homes in order to discourage real estate investment.From Bernie's Website"When Bernie is president, he will:Create an office within the Department of Housing and Urban Development to coordinate and work with states and municipalities to strengthen rent control and tenant protections, implement fair and inclusive zoning ordinances, streamline review processes and direct funding where these changes are made.This office will convene key leaders, academics, experts, local officials, renters, tenants, and homeowners to create and implement these necessary solutions.Preempt laws that prevent inclusionary zoning for luxury developments.End exclusionary and restrictive zoning ordinances and replace them with zoning that encourages racial, economic, and disability integration that makes housing more affordable.Require that recipients of federal funding from the Department of Transportation and the Department of Housing and Urban Development make these important zoning reforms.Provide funding to states that preempt local exclusionary zoning ordinances to make housing more equitable, accessible and affordable for all.Make federal funding contingent on creating livable communities.Encourage zoning and development that promotes integration and access to public transportation to reduce commuting time, congestion and long car commutes.Prioritize projects that reduce greenhouse gas emissions, create walkable and livable communities, and reduce urban sprawl.Encourage zoning and development designed to expand and maximize the number of units fully accessible to people with disabilities.Place a 25 percent House Flipping tax on speculators who sell a non-owner-occupied property, if sold for more than it was purchased within 5 years of purchase.Impose a 2 percent Empty Homes tax on the property value of vacant, owned homes to bring more units into the market and curb the use of housing as speculative investment.Encourage “circuit breakers” on property taxes to protect homeowners in gentrifying neighborhoods from being priced out of their own homes as their property values rise.READ MORE: https://berniesanders.com/issues/housing-all/From my point of view, anything that impedes or obstructs REI's cash flow is a bad thing.

If an extra $80/mo on a hundred thousand property is going to make it a bad deal (reduced year after year, and BONUS, more of those tax deductions you were looking for.) then it’s a bad property to buy. 

With hard money you have fewer dollars in the deal and therefore increase your IRR dramatically (and in some cases reduce your risk).

It sounds like you might be renting to a family member for reduced rent.

That's because insurance companies consider the fair rental value of the unit and reduce the check by any avoidable expenses.

Structural engineering could be done prescriptively, however with the high wind and slow loads and mountainous siting, I am leaning toward using an engineer I've worked with on many projects before for a reduced rate, say 2k.

Chris Of all the banks I have gone to - small / big / coops - you have a selected who do financing on investment properties and than if they are condos and are nowarrantable the number reduces further.