It seems most of the HOA's have figured out the insurance issues from the past couple of years and have leveled out their HOA fees and insurance assessments.

I'm currently living in one side of the duplex and planning to rent out the other side.

If I can score some cash flow, I'll take the win, but my plan is to at least break even in payments.

It simply means risk adjusting portfolio for actions of making it liquid for end of life planning.

We plan to use the home currently for about maybe 2 months out the year and would like to rent it out the remainder of the year on Short term rental.

Want to impress clients/banks/investors then put together a great business plan and come in with some numbers that work.  

Shawn - I would suggest you develop a pro forma based on the stabilized state of the property to understand if it cash flows once all units are occupied being sure to include all reasonable revenue assumptions (rents, vacancy factor, etc..) as well as expenses (debt payments, maintenance, utilities, property management, taxes, insurance, turnover costs, etc..)

Pushes the cost of damage protection insurance onto the hosts and guests.

Hello Group I have a short term rental in the Santa Cruz area that I am looking to get homeowner's insurance on. 

I know that searching for financing sooner than that is appealing, but the best rates that I have seen all require closing after 90 days of ownership.I will usually kick things off around day 60 of ownership and plan to close within four weeks of that.