Additional info to help the discussion: Rent growth year over year:Appreciation Growth Calculator (Conservative 3%) Scenario: Total cash in deal from Investor: $29,010Investor Contribution: 100%My contribution: 0%Goal: Figure out how in 5 years, I now own 100% of this property.

Any suggestions on insurance companies that specialize in Homeowner Insurance for investors that have a part-time vacation home that also serves as a rental property?

Or does anyone have any other suggestions? 

I’d suggest reaching out to the county’s tax assessor office and asking them those questions.

Do you find it's worth the higher cost and additional hoops to jump through?

Additionally, I'd suggest joining CT RE groups on Facebook.

@Melanie Hernandez - If you want to see whether or not an Airbnb location will be profitable or not I would suggest you look at Airdna or Mashvisor. 

@Noah Condon I would suggest you learn about hard money financing, unless you have unlimited cash. 

They then suggested a WY LLC instead.

“Keep in mind the good thing about targeting MF 2-4 units is that for each door you’re getting an additional rent per month.